Real Estate Rookie – "How to Buy Your First (or Next) Rental Property in 2026 (Step by Step)"

Hosts: Ashley Kehr & Tony J. Robinson
Date: February 18, 2026

Episode Overview

This episode of Real Estate Rookie is a comprehensive, actionable blueprint for anyone looking to purchase their first, second, or third rental property within the next 90 days. Targeted directly at new or "rookie" investors, Ashley and Tony walk listeners step-by-step through the process, from clarifying your goals and financial foundation to making offers, closing, and finally managing your new investment.
They pull from Ashley's book, "Real Estate Rookie: 90 Days to Your First Investment," but deliver the roadmap in an approachable, week-by-week checklist with lots of personal experiences and practical tips.

Key Discussion Points & Insights

1. Laying the Foundation

(Starts ~00:36)

• Clarify Your Why:
  Ashley emphasizes that before analyzing or finding deals, you must get clear about why you want to invest in real estate.
  "You need to set your foundation and you need to understand why you're investing in real estate. What is your goal? What do you want out of it?" – Ashley (00:47)

• Personal Finance Prep:
  Know your capital sources and have a solid grip on your finances. Utilize budgeting tools (Ashley recommends Monarch Money) for a full financial picture.

• Rank Your Priorities:
  Tony explains the core motivations in real estate—tax benefits, cash flow, and appreciation—and recommends ranking what matters most to you, since few deals maximize all three. "It's important as you're getting started to understand what is it that I'm trying to optimize for..." – Tony (02:13)

• Action Item:
  Block out 2–3 hours to write out your goals, motivations, and plan, either on paper or digital doc. This visioning step is foundational.

2. Choosing Strategy & Niche

(Starts ~04:06)

• Asset Class & Strategy:
  Decide what type of property (single family, small multifamily, condos, mobile/manufactured, etc.) and strategy (flipping, long-term rental, short-term rental) fit you best. "Identifying what type of property you want to buy, and then what's your strategy that you're going to layer on top of that specific niche." – Tony (04:06)

• Buy Box Creation:
  Use the "buy box" resource from BiggerPockets to define specifics (property type, price, location, etc.) for your ideal purchase—this narrows focus during deal analysis.

3. Selecting & Researching Your Market

(Starts ~05:40)

• Avoid "Goldilocks Syndrome":
  Don’t get caught searching for the "perfect" city; there are hundreds of viable markets. Start with a few that align with your goals. "There are 20,000 plus different cities... chances are there's not just one city that's the best... There are hundreds, if not thousands..." – Tony (05:40)

• Use Data:
  Access tools like the BiggerPockets "Find a Market," Neighborhood Watch, Bright Investor, and even ChatGPT for data (job growth, rents, taxes, landlord/tenant laws).

• Validate With Your Strategy:
  What works for one investor or strategy might not work for another; don’t blindly copy social media trends—verify based on your own plan.
  "Just because you're going to go, it works for somebody else in a market doesn't mean that it's going to work for you." – Ashley (07:36)

• Memorable Moment:
  Lighthearted banter about luxury short-term rentals next to manure-laden farms adds warmth and humor to the conversation.
  "Do you want fresh manure or liquid manure? There's two different." – Ashley (08:50)

4. Practicing Deal Analysis

(Starts ~09:17 and 14:52)

• Analyze Listings Early:
  By week 4, start analyzing 5–10 active listings per week in each chosen market. Even if a property isn’t a real candidate, practice builds skills.

• Track & Spot Patterns:
  Use calculators and spreadsheets to document deal outcomes and spot what works or doesn't in your market.

• Challenge: "30 Deals in 30 Days":
  Tony issues a challenge—analyze one deal per day for a month to accelerate learning and increase chances of finding a winner. "I like the idea of 30 deals in 30 days... Most people do not find deals simply because they're not analyzing or underwriting enough." – Tony (14:52)

• Watch for Overlooked Expenses:
  Consider market-specific costs (e.g., snow plowing, pools) and check with local investors for non-obvious but critical expenses.
  "That's where it pays to go into BiggerPockets forums, Facebook groups, to ask in the market that you're investing in, what are some other expenses that I'm not aware of?" – Ashley (16:33)

5. Building Your Team

(Starts ~20:19)

• Key Team Members:
  Lender/private money source, real estate/wholesale agent, attorney (especially in attorney-close states), title company, insurance agent, handymen, property managers.

• How to Find Them:

  • BiggerPockets Team Finder/tool
  • Ask for referrals in investor communities
  • Social media – your friends may surprise you
  • Spreadsheet or photo albums to track contractor contacts

• Start Early:
  It’s not too soon to contact potential team members—let them know your intentions and begin building relationships before you have a deal.

  "Just call them, let them know what you're trying to do and that you're looking for a handyman to take care of a property once you get in under contract and see if that's even something they'd be interested in." – Ashley (21:50)

6. Making Offers and Negotiation

(Starts ~23:15)

• Get Comfortable Making Offers:
  Don’t fear low offers—it's part of the business. "The worst thing that has happened with making a low ball offer is that they just say no and that's it." – Ashley (23:36)

• Don’t Fixate on List Price:
  Sellers often list high expecting negotiation. "The biggest mistake that rookie investors make is that they take whatever the listing price is as the lowest acceptable price..." – Tony (25:00)

• Action Item:
  If numbers don’t work, lower your offer. Submit lots of offers—volume increases your odds.

  "When we were super, super heavy in acquisition mode, I would send my agent 10 to 15 properties with my offer price attached... majority would say no, but every once in a while I get one that says yes." – Tony (25:00)

7. Under Contract: Due Diligence to Close

(Starts ~28:00)

• Inspection & Financing:
  Always do an inspection. Work out insurance and finalize your loan with the lender.

• Tenant Estoppel Agreements:
  Essential if tenants are in place—verify what the seller says with the tenants directly. "You don't want to buy a property, find out the seller said the tenants are actually paying $1,000 per month, but then...no, I pay $500." – Ashley (29:35)

• Utility Transfers:
  Arrange for utilities as per lease (your name or tenant's).

• Prepare for Ownership:
  Plan for property management, set up software, arrange renovations or hand-off to a manager. Use the closing checklist available from BiggerPockets.

• Be Ready to Walk Away:
  The inspection/due diligence period exists so you can renegotiate or exit if things aren’t as advertised. "Don’t be afraid to walk away from the deal during this period...do not get so emotionally attached to the first offer that you've actually gotten accepted that you end up stepping into a deal that doesn't make sense long term." – Tony (30:46)

8. Post-Closing: Operations & Scaling

(Starts ~31:10)

• Celebrate—but keep working:
  Manage your property (or manager), communicate with tenants, possibly furnish, and continue improving processes. "This is where the fun begins, the real work begins. And you are now a real estate investor." – Ashley (31:10)

Notable Quotes with Timestamps

• "A lot of rookies aren't stuck because they don't know enough. They're stuck because they don't know what to do next." – Tony (00:04)
• "You need to be able to know where your capital is coming from. You need to understand finances, because a lot of investing is finance." – Ashley (00:47)
• "The goal isn't to necessarily identify the one city that is the absolute best for you. The goal is to identify multiple cities that align with your goals..." – Tony (05:40)
• "If you're analyzing deals and it looks like no deals are, are working for you, try lowering the purchase price. That's the easiest thing to manipulate..." – Ashley (23:36)
• "Don’t be afraid to walk away from the deal during this period either. If things come up during your inspection, during your due diligence. That is the entire reason that a due diligence period in a contract is to give you the ability to either renegotiate or walk away from the deal." – Tony (30:46)
• "This is where the fun begins, the real work begins. And you are now a real estate investor." – Ashley (31:10)

Episode Roadmap: Timestamps for Major Segments

| Segment | Timestamp | |--------------------------------|-------------| | Laying Your Foundation | 00:36–05:05 | | Choosing Market | 05:40–09:17 | | Practicing Deal Analysis | 09:17–14:52 / 14:52–20:19 | | Building Your Team | 20:19–23:15 | | Making Offers & Negotiation | 23:15–25:52 | | Under Contract, Due Diligence | 28:00–30:46 | | Post-Close Operations | 31:10–end |

Tone & Language

The hosts are pragmatic but warm and encouraging—never condescending, always rooting for rookies to succeed, and unafraid to make real-world jokes or share their own struggles. There’s a focus on demystifying the process, giving listeners explicit action steps, and providing emotional support for the moments when progress stalls.

Final Takeaways

• Progress comes from consistent action and building skills, not just consuming information.
• Don’t get stuck trying to be perfect; momentum is everything.
• Analyze, offer, negotiate, and build relationships early and often.
• Use the tools and resources available, and seek out community (online and local).
• Celebrate your wins, but know that every deal is a step on a longer journey.

For a more detailed roadmap or to find resources/tools mentioned, visit the BiggerPockets Resource Hub.

Hosts: Ashley Kehr & Tony J. Robinson
Podcast: Real Estate Rookie
Episode Title: How to Buy Your First (or Next) Rental Property in 2026 (Step by Step)
Release Date: February 18, 2026