I’m Buying Land to Build Rentals…But Should I? (Rookie Reply)

Summary

Podcast Summary: Real Estate Rookie - Episode: “I’m Buying Land to Build Rentals…But Should I? (Rookie Reply)”

Release Date: July 18, 2025

Hosts: Ashley Kehr and Tony J. Robinson
Guest Mentioned: Katie Neeson (past guest)
Platform: BiggerPockets
Description: The Real Estate Rookie podcast serves as a personal trainer for aspiring real estate investors, offering detailed breakdowns of real-world deals, coaching sessions, and a supportive community. Hosts Ashley Kehr and Tony J. Robinson address beginner questions to help listeners embark on their journey toward financial freedom through real estate.

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Introduction

Ashley Kehr and Tony J. Robinson kick off the episode by introducing the focus of today’s “Rookie Reply” segment: three pivotal decisions facing rookie real estate investors.

• Ashley Kehr [00:00]: Highlights the three main topics:

  1. Structuring a land development project.
  2. Investing in short-term rentals for personal enjoyment.
  3. Whether to cash out a retirement account to purchase the first property.

• Tony J. Robinson [00:18]: Emphasizes the importance of these questions in evaluating risk, return, and the utilization of existing funds.

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1. Structuring a Land Development Project

Question from Alora [00:37]: Alora seeks advice on purchasing land with an abandoned home. She outlines two options:

• Option 1: Develop an eight-unit property, which promises better long-term returns but requires substantial capital.
• Option 2: Subdivide the land into three single-family lots, build on one, sell it, and use the proceeds to develop the remaining two lots. This option is more manageable financially but offers lower long-term gains.

Discussion:

• Tony [01:23]: References past podcast guest, Katie Neeson, who specializes in redeveloping lots with abandoned homes into multifamily properties. He probes Alora’s experience in development to assess her capability to handle an eight-unit project.

  “If the deal is good enough, go shop it around to folks and see who might be interested in doing it with you.” [01:50]

• Ashley [02:55]: Emphasizes the need to evaluate long-term financials and personal goals. She questions whether managing an eight-unit property aligns with Alora’s aspirations compared to owning a single-family home free and clear.

  “Do you want to manage an eight-unit property, do you want to have partners or vice versa?” [04:20]

• Tony [05:10]: Introduces the importance of local city preferences and potential incentives. Citing Katie Neeson’s experience, he suggests consulting with city officials to explore grants or tax abatements for larger developments.

  “Maybe they give you some kind of grant or tax abatement or whatever it may be if you go and build that unit out.” [05:40]

• Ashley [06:04]: Agrees with Tony, noting the value of engaging with town employees to understand available support, thereby enhancing the viability of larger projects.

  “Katie has made those deals work because she is going to the town and seeing what they want instead of her telling them this is what I’m gonna do.” [06:30]

Conclusion: Alora should assess her development experience, financial capacity, and personal management preferences. Exploring partnerships and local incentives can make the eight-unit project feasible if it aligns with her long-term investment goals.

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2. Investing in Short-Term Rentals vs. Single/Multi-Family Homes

Question from Sean [08:43]: Sean is remodeling his primary residence to rent it out and is contemplating whether to invest in:

• Single-family homes.
• Multi-family homes.
• Short-term rentals in the Ozarks that he can enjoy personally.

Discussion:

• Ashley [08:43]: Outlines the financing implications of each option, such as living in one unit of a multifamily property or renting out rooms in a single-family home. She raises concerns about mortgage stipulations related to short-term rentals for primary residences.

  “Do you want to put in that much work to actually do that? Do you want to learn everything that goes into developing a multifamily property?” [11:00]

• Tony [10:21]: Admits to limited personal experience with short-term rentals as primary residences but suggests consulting with loan officers regarding any mortgage restrictions. He introduces alternative financing options like the 10% down second home loan.

  “If you do go to the short term rental route, there's the 10% down second home loan which is still an option.” [10:50]

• Ashley [11:03]: Encourages Sean to consider both financial and emotional factors, such as cash flow and personal lifestyle preferences. She advises running detailed numbers for each investment type and evaluating long-term implications.

  “This definitely has an emotional play to it. Do you have a preference like if it's a single family home and you're going to live there, you know, and house hack the rooms or something like that.” [11:20]

• Tony [12:52]: Reinforces that the decision should align with Sean’s personal goals and preferences. He suggests that Sean doesn’t have to choose exclusively between options and can diversify his investments over time.

  “Maybe the first deal is a short term rental in the Ozarks, and then maybe your next deal is a single family home or the small multifamily.” [13:10]

Conclusion: Sean should evaluate both the financial returns and personal satisfaction each investment type offers. By running comprehensive financial analyses and considering personal lifestyle choices, he can determine the best path forward. Diversifying investment strategies over time is also a viable approach.

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3. Cashing Out a 401(k) to Purchase First Property

Question from Jared [17:45]: Jared has $28,000 in savings and a 401(k) worth $40,000. He considers:

• Using $28,000 from savings.
• Cashing out $40,000 from his 401(k), which after penalties would leave him with approximately $28,000.
• His plan is to rebuild the 401(k) through property cash flow and savings.

Discussion:

• Tony [17:45]: Suggests that Jared should prioritize saving more capital instead of cashing out the 401(k), as a withdrawal might not significantly impact the investment capability.

  “Maybe let's just wait and pause.” [18:15]

• Ashley [19:24]: Advocates for not touching the 401(k) due to penalties and the benefits of letting it grow. She proposes alternative strategies:

  1. Taking a Loan Against the 401(k): Borrowing up to 50% of the balance without incurring taxes or penalties.

     “The interest you're paying is just going back to you.” [19:50]

  2. Rolling Over to a Self-Directed IRA: Allows investment flexibility, such as partnering in syndications without directly funding deals.

     “I used equity trust, which is a great partner of BiggerPockets.” [21:10]

  3. Comparing Investment Returns: Analyzing the 401(k)'s performance versus potential real estate returns to make an informed decision.

     “Compare what would be your return on investment in the stock market or if you put that money into a property.” [22:00]

• Tony [23:32]: Highlights the variety of financing options beyond the 20% down payment Jared assumes is necessary, such as:

  • House hacking with FHA loans (3.5% down).

  • VA loans (0% down for veterans).

  • Investor loans with lower down payments.

    “You have to think a little bit more creatively with your solutions.” [24:00]

    “If you could only tap into the 28k, what options would we have?” [24:10]

Conclusion: Rather than cashing out his 401(k), Jared should explore alternative financing methods and investment strategies that do not jeopardize his retirement savings. Utilizing a 401(k) loan or rolling over to a self-directed IRA, combined with creative financing options, can provide the necessary capital without incurring significant penalties or taxes.

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Conclusion

Ashley [25:44]: Emphasizes the importance of personalized decision-making based on individual financial situations, timelines, and risk tolerance.

“There's no one size fits all answer. It's about being honest with yourself about your financial situation, your timeline, and how much you're willing to stretch.” [25:50]

Tony [23:32]: Reinforces that real estate investing offers diverse pathways and encourages investors to think creatively beyond conventional methods.

“What we’re doing is figuring out how to make your money work harder, what kind of property fits your goals, and how much risk you’re actually willing to take.” [24:30]

Ashley [25:44]: Wraps up the episode, thanking listeners and inviting them to join future episodes.

“Thank you guys so much for joining us for this episode of Rookie Reply. I'm Ashley, he's Tony, and we'll see you guys next time.” [25:50]

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Key Takeaways:

• Land Development: Assess development experience, financial capacity, and explore partnerships and local incentives.
• Short-Term Rentals vs. Traditional Rentals: Balance financial returns with personal lifestyle preferences and consider flexible investment strategies.
• Retirement Funds: Avoid cashing out retirement accounts; explore loans or self-directed options and leverage creative financing methods.

Notable Quotes:

• “If the deal is good enough, go shop it around to folks and see who might be interested in doing it with you.” – Tony J. Robinson [01:50]
• “Do you want to manage an eight-unit property, do you want to have partners or vice versa?” – Ashley Kehr [04:20]
• “Maybe the first deal is a short term rental in the Ozarks, and then maybe your next deal is a single family home or the small multifamily.” – Tony J. Robinson [13:10]
• “There's no one size fits all answer. It's about being honest with yourself about your financial situation, your timeline, and how much you're willing to stretch.” – Ashley Kehr [25:50]

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This episode of Real Estate Rookie delves into critical decision-making processes for new investors, offering practical advice and encouraging a thoughtful approach to building a real estate portfolio. By addressing real questions from listeners, Ashley and Tony provide actionable insights tailored to varying investment goals and circumstances.

Transcript

[Ashley Kerr]

On this rookie reply, we're talking through three big decisions rookie investors are facing right now. How to structure a land development project, whether to invest in short term rentals you can also enjoy, and whether to cash out a retirement account to buy your first property.

[Tony J. Robinson]

These are real questions from real investors just starting out and they hit on some of the most important things you'll have to weigh when getting started, like risk return and how to use the money you already have.

[Ashley Kerr]

This is the Real Estate Rookie podcast and I'm Ashley Kerr.

[Tony J. Robinson]

And I'm Tony J. Robinson. And with that, let's jump into question number one, which comes from Alora in the BiggerPockets forum. So this question says I have the ability to purchase a great piece of land with an abandoned home. The parcel as it sits allows for an eight unit to replace it, but we don't have the cash for anything like that. The secondary option is to divide it into three lots of build on one sell and then use that money to develop the other two. The three lots would only be approved for a single family. Obviously the eight unit makes the most sense for long term money. We just don't have the capital for a project that large yet. I also haven't taken on that large of a multi unit build. Would you make do with the option you have of subdividing and building? Would you build a smaller multifamily unit on the lot instead?

[Ashley Kerr]

What?

[Tony J. Robinson]

Would love to get insight from others on how they would handle it. Interesting situation to be in, you know, to have the lot abandoned home. It reminds me of Katie Neeson who we've had on the podcast and that's pretty much her entire strategy where she goes around looking for lots with abandoned homes or lots where abandoned homes used to be and then she redevelops them into, you know, typically larger properties, multifamily townhomes that she sells off, whatever it may be. So there's obviously a business case here that's to be made. So allure says in the question, I also haven't taken on that large of a multi unit build, but does that mean that you've done some sort of development in the past? Because that's kind of what I'm picking up, that you've done some development but just not that big before. I think the question is how confident are you in a your ability to execute on that eight unit deal? I get that it's new, but is it like a sequential next step where maybe you've built a duplex or a triplex and eight units is just like that next move or have you only built, you know, maybe one single family home and this is an 8x bigger job than we ever done before. But if this is like the logical next step for you and the numbers are like really, really good and which it sounds like it Is in the 8 unit, then maybe this is an opportunity for you to go out and partner with someone. Can you raise capital from folks and say like, hey, here are the numbers on the bills I've done in the past. Here's what I'm projecting for this 8 unit. Do want to come in on this with me? Because if the only thing holding you back from doing the eight unit is the capital, I think if the deal is good enough, go shop it around to folks and see who might be interested in doing it with you.

[Ashley Kerr]

I also want to know too the, the numbers on this and if the numbers have actually been run for long term because it says like, obviously the long term play is better if you have the eight unit. But that is that just based off the fact of like, wow, I'll get to own eight units and hold, hold them. And that's better than me only having one lot left after I sell off the other two. And really that then if you run the numbers, it maybe could be that the lots are better because you could take that capital. And this is a lot of Katie Neeson's model is that she gets her lot in her building for free after selling off the other two lots and owns that property for free. So would you rather have an eight unit with a debt on it and maybe a partner? So you don't even own 100% or own a building free and clear because you sold off the other two and even though it's one unit or you know, it's still a free and cleared property. So I think you need to know more of your why also because even if the number is slightly better on one or the other, do you want to manage an eight unit property, do you want to have partners or vice versa? Do you want to own a single family home or do you only like multi family? But this is a unique situation you take on the single family. So I think there's a lot more to look at than just like, oh, an eight unit is better than me ending up with one unit. So I think really take that comparison and play as to also, what does it take to develop the eight unit? Do you want to put in that much work to actually do that? Do you want to learn everything that goes into developing a multifamily property. I did six patio homes before and it was completely different than doing construction of a single family home. And you have to do a swip report, you have to. There's so much more that goes into the commercial development of things, approvals, inspections, things like that. But if you already have some kind of development experience like this could just be the next step up for you and maybe it's, it's time to, to level up if, if that's what your goal is, to be able to do that.

[Tony J. Robinson]

I think one other piece to include in the, the decision making here is what does your city prefer? And when Katie was on the podcast, she shared a story where the city gave her. I can't remember the exact amount, but it was like a good amount of money towards her project because she was helping the city execute on their plan of, of beautifying the streets of, of Bryan, Texas. And it's like if, if your city maybe has some sort of incentive to say like hey, we would actually love an 8 unit apartment building here because it, it helps our, you know, 10 year plan of bringing more affordable housing, whatever it may be. Maybe they give you some kind of grant or tax abatement or whatever it may be if you go and build that unit out. So I think talking to the city and, and saying hey, do you guys have a preference of three single family homes or one eight unit apartment complex and see which one they prefer?

[Ashley Kerr]

Yeah, that is such a great idea because there are so many grants or like especially smaller towns where you get to go and actually sit down and talk to the town employees, the building inspector, the clerk and actually ask those types of questions. But yeah, that is a, a big way that Katie has made those deals work is because she is going to the town and seeing what they want instead of her telling them this is what I'm gonna do. And I guess she does say sometimes this is what you're gonna give me if I'm gonna. She's very good at demanding and commanding. Okay, well we have to. We're gonna take a quick ad break and when we come back we're gonna talk about investing and short term rentals. We'll be right back.

[Aaron]

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[Ashley Kerr]

Okay, welcome back from our short break. Our next question is from Sean. I'm in the process of remodeling my primary residence to rent it out. I love to travel and have thought about short term rentals in the Ozarks since I love it there and it's close to me. My question is should I stick with some single family homes or multi family homes first or should I use my equity to buy short term rentals that I could see stay at throughout the year? What a cool position to be in. You know, be able to decide. I got three different types of strategies I can do and you know each of these come with their own pros and cons. I guess like one big piece for to differentiate these is the financing piece. So if you're going to Buy something as your primary residence, a multifamily, you can live in one unit, rent out the other units. A single family, you could live in it and then rent out the rooms. If you're going to use that primary residence financing on it, you do have to live in the property for most loan products for at least a year. There are some circumstances where you can get out of that year criteria. But if you're going to do your property as a short term rental. Tony, are there any like stipulations of like if it is your primary home, how much you rented out where like it would be like mortgage fraud because you're renting it out as a short term rental even though you stay there X amount a year and it's the only property you own as like your primary residence.

[Tony J. Robinson]

I actually don't know because I've never done it that way where I've, I've purchased it as a primary with the intention of short term renting it when I'm not there. I would assume there's some sort of stipulation if it's like a primary home mortgage around how often you can rent it out. So I would probably point that back to, you know, whichever loan officer or bank that you're working with to get the debt. But if you do go to the short term rental route, there's the 10% down second home loan which is still an option. A lot of lenders still offer this so maybe you're not getting the, you know, the three and a half or the 5% down with the primary residence. But 10% is not, you know, it's not too far off. So I think there's still some other options there to get you in for a lower down payment than like a, you know, 20 or 25% type down payment?

[Ashley Kerr]

Yeah, and I think this one like has a lot of emotional versus financial. I think as long as you like run the numbers on each property and it's a cash flowing deal or you're living for free as a house hack, then I don't think you can go wrong. And I wouldn't scrutinize over which one of these different strategies is going to give me the best return. Like maybe if the short term rental income potential just blows the single family out of the water, then yes, do that. But since this is going to weigh a lot on how you live, this definitely has an emotional play to it. Do you have a preference like if it's a single family home and you're gonna live there, you know, and house hack the rooms or something like that. Is that actually something you want to do or would you rather, you know, make a little bit less money each month or pay a little bit more to live in a house hack where it's separate units? So I think you definitely have to take that into consideration. As much as I'd love to give you an answer of like, do this one, there's. You have to look at the markets. Okay, so what you said, the Ozarks for a short term rental, what market would you do? The single family, the multifamily. What does the appreciation look like in those properties or in those markets? What would your cash flow be for each of those? So really run the numbers for each. Run the numbers today, what they look like. Run the numbers with you living in each of these properties, what it looks like for the next year and then once that year requirement is done, what does the property look like as a long term rental? Renting out both units if it's a duplex, or converting it fully to a full on short term rental all year round?

[Tony J. Robinson]

Yeah, I think you hit the nail on the head, Ash. Like, I think it's hard for us to give a definitive answer about what option makes the most sense. But I think at the end of the day, you know, Sean, the person who asked this question, it's just like, what's, what do you want? You know, like, like what makes you more excited in terms of an investment? Is it a single family home that's maybe lower maintenance and steady cash flow? Or is it the idea of having a vacation home in the Ozarks you can go visit? And I think if you weigh those two of like, hey, what actually do I want more? What helps me achieve the goals that I have in mind? I think it'll become a little bit more apparent. But the truth is that you also don't have to choose between one or the other. Like, maybe the first deal is a short term rental in the Ozarks, and then maybe your next deal is a single family home or the small multifamily. So don't feel that choosing one means that, that there's no opportunity to do the other. It's just which one's going to come first. And I think that just comes down to personal preference.

[Ashley Kerr]

And Tony, is this Sean, your son? Is he starting to remodel his room for one of his baby sisters to move into and he's trying to figure.

[Tony J. Robinson]

Out where he's, where he's going? Yeah. Hey, I would be super proud if he's got a home somewhere that I don't know about that he's in the middle of remodeling. So maybe, maybe one day.

[Ashley Kerr]

Okay, we're gonna take our last break and we'll be back with our last question right after this.

[Tony J. Robinson]

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[Tony J. Robinson]

Right guys, so we're back here with our last and final question for today. This question comes from Jared and Jared posted this in the BiggerPockets forums and he says we have $28,000 in savings and are looking to get into multifamily investing with a 20% down payment needed. I've thought about cashing out my 401k, which is worth around $40,000. I know the penalty will leave me with around $28,000 after taxes. I feel like there are more potential gains in real estate than leaving it in my 401k. I'm 35 and would plan to rebuild the 401k using property, cash flow and savings. Should I cash out my 401k to buy my, my first property. So just for context here, $28,000 in cash, another $28,000 sitting in a 401k or at least that you get after penalties and whatnot. So what is that a total of $56,000 they'd have access to, to go out there and get that first deal? I think my initial gut reaction is I would just focus on either a saving more capital. And I know that's, that's not like the sexy answer and you know, it's maybe not what, what Jarrett wants to hear, but I think that might be my first move because real estate investing does get easier if you have more capital to work with, just like point blank period. And the 40k that's in your 401k, I mean, I don't know if it's really going to move the needle a ton to go from 28 to 56 or if it's worth, I think, the 28k to take it out of your account. If you're able to get like 200k from your 401k, I think maybe it makes a little bit more sense. But it's like how long would it take for you to save up that 28k without having to tap into your 401k? So my initial gut reaction is like, maybe let's just wait and pause. But I don't know. Ash, what's your initial take?

[Ashley Kerr]

I always had this mindset of you, like, you don't touch your 401k. Like you leave it, you let that grow. That's like you're diversified. You have the 401k. And I was just like, I don't know if it was just how I was brought up, even though I don't think either of my parents had 400ks because they were both self employed. But I just, that was just always a mentality. You leave the 401k alone. You don't touch it. The penalties and fees to withdraw from it do, like, make me see sick thinking about like that much money gone right away. What I would first look at is doing a loan, taking a loan against your 401k. A lot of employers offer this where it's Usually, I think 50% of whatever your balance is in your 401k is what you can take out as a loan or up to $50,000. I'm not completely sure on this. Ask your plan provider what, what it is, but that's, I'm pretty sure that's it. So in this case, you would be able to take out $20,000 as a loan every week or whenever you get a paycheck, a small amount is paid back to your 401k. So the con of this is your money is no longer invested into the 401k. The Pro is you're paying interest, but you're paying interest back to yourself and it's being reinvested back into your 401k. So that I think could be kind of like a compromise instead of paying those taxes and penalties is pulling your money out because you're not going to invest it anyways in the stock market if you're just going to cash out and put it in real estate. So I would borrow against that. The interest you're paying is just going back to you. You're paying interest to yourself. It's not like to a bank or anything. So I would look at that, that circumstance first. The next thing I would do is what I did was, and this was for an old employer though, I took the 401k from that and I moved it into a self directed ira. So that way I can deploy the funds however I want. So there are a lot of rules like I can't go out and buy my own deal and use the funds from the self directed ira to actually fund that deal. It would have to be somebody else's deal where I'm hands off from it. So, so maybe there was somebody else that had a deal, you were going to be passive in it, whatever. You could go ahead and partner with them. Invest in a syndication is a great one that some people use their self directed IRA funds for. And that's just doing a rollover where you're not paying fees. I used equity trust, which is a great partner of bigger pockets and it was the easiest thing I've ever done. I thought it really was going to be a lot more difficult to actually roll over my 401k into a self directed IRA. And then having to actually deploy my funds from the self directed IRA into the investment was very easy too. They walked me through the whole process. So I think that there is, there's other options for you besides just cashing out. And the third thing I would look at is what, what return has your 401k been getting you? What does the performance of it look like? What, what are the fees that you are paying if you're not solely invested in index funds? Those fees are probably pretty large that you're paying to have your 401k managed and for the fund fees that you're paying and Then I would compare that to what kind of deal are you looking at and what would be the return of your money. So compare what would be your return on investment in the stock market or if you put that money into a property, if you did pull it all out and run those numbers and see how they kind of play out. Obviously you can't predict the performance of the stock market and say, like, oh, but you can look back on average what's been the performance of the portfolio and kind of use that as an average. And the same with real estate. Real estate could crash. There could be great appreciation and you sell your property and you make 50% on your money, whatever, in just one year. So you don't know, but at least you can kind of run the numbers to project which is the better return.

[Tony J. Robinson]

Yeah, you bring up a lot of good points, Ashley. And, you know, the 401k is a contentious topic on, like, Reddit. You know, like, there's some people who think the 401ks are like, you know, America's been scammed into this idea of the 401k. And obviously there's a lot of people who have made a tremendous amount of wealth in their life using 401k. So I think the idea to participate or not participate is somewhat of a personal choice here that, you know, you'll have to make for yourself. But I think the mistake that a lot of rookies make is they paint themselves into a corner because they have such a narrow scope on the decisions that they're making. And what I mean by that is, Jared, you said, like, I have 28k and I need 20 down. That is not a factual statement because there are a ton of other ways to start investing in real estate that do not require a 20 down payment. You could house hack a small multifamily FHA, 3 1/2% down, conventional 5% down. Something like NACA, 0% down. If you're a veteran, 0% down. The VA loan. So you get house hack with significantly less than 20% down. There are investor loans. Again, we had Jeff Welgan on episode 588. They're 15% down. Investor loans you could go get that are not 20% down. We just interviewed Joe Pizzuli on episode 584 and it cost him $0 out of pocket to get his first deal. His he worked with the small local bank who funded the purchase and the renovation, and he came out of pocket with $0. And you could do the same thing. And now your 28k becomes your reserves for that property when you get started. So, again, I think the mistake, Jared, that a lot of new investors make is that they have this idea of what real estate investing is. But the more you start to peel back those layers, you start to realize that there are so many other ways to get started. So if you're dead set on investing in real estate, I would challenge you to say, okay, how can we invest with the 28k that we have? What is the smartest move for us to make with the 28k? And I think as you start to think through it in that way, like, hey, if we could only tap into the 28k, what options would we have? It'll force you to get a little bit more creative with your. With your solutions. So these are the kinds of big decisions every investor has to face at some point, right? Figuring out how to make your money work harder, what kind of property fits your goals and how much risk you're actually willing to take.

[Ashley Kerr]

And remember, there's no one size fits all answer. It's about being honest with yourself about your financial situation, your timeline, and how much you're willing to stretch. Thank you guys so much for joining us for this episode of Rookie Reply. I'm Ashley, he's Tony, and we'll see you guys next time.