Real Estate Rookie – Deal of a Lifetime? How to Structure a Win-Win Seller Financing Deal (Rookie Reply)

Hosts: Ashley Kehrick & Tony J. Robinson
Date: January 2, 2026
Podcast: BiggerPockets Real Estate Rookie
Episode Theme:
How rookie investors can navigate the current real estate market, with a focus on structuring creative deals—especially within families (like seller financing and trusts)—plus advice on where and how to buy when getting started.

Episode Overview

This episode delivers practical guidance for new real estate investors facing questions around high interest rates, buying from family, and choosing profitable markets. Ashley and Tony answer listener questions from the BiggerPockets forums, diving especially deep on structuring "win-win" seller financing deals in family situations and the importance of aligning any decision with your ultimate investing goals.

Key Discussion Points & Insights

1. Should You Wait Out High Interest Rates or Buy Now?

(00:26–04:38)

• Listener "Trevon" from Georgia asks if he should buy his first rental property with current high rates, or hold off for a better deal.
• Ashley’s Take:
  • Don’t be paralyzed by higher rates—deals still exist.
    • “Don’t get caught up on not buying just because interest rates are high right now. Who knows when interest rates will be back down to 3, 4%, if ever, right?...That is a really big opportunity cost that you would be missing out on. Not getting a deal now, waiting to time the market perfectly.” (03:49)
  • Analyze multiple deals (recommendation: 5–10 per day) to get a real sense of cash flow potential.
  • The market is more negotiable now compared to the “hot” low-rate years.
• Tony’s Take:
  • Investors need to define their goals: cash flow vs appreciation vs diversification.
    • “What are you actually trying to optimize for here?...If it is cash flow and you feel like it's really slim on this deal...then yes, by all means, don't pull the trigger on this one. Go search for something else.” (03:28)
  • Don’t compare today to “unicorn” 3% rates—they’re not coming back soon.

2. Navigating Family Sales & Seller Financing

(06:42–13:57)

• Listener "Matt" considers taking over two 8-unit properties in Philadelphia from an elderly family member who’s open to discounted pricing, seller financing, or a trust arrangement.
• Key Issues:
  • Deferred maintenance ($200K–400K needed).
  • Seller wants either a lump sum, annuity, or continued income.
  • Matt is a newbie, based in DC, with considerable liquidity ($250K cash, $1.4M LOC at 6.5%).
• Tony’s Strategy:
  • “I don't really see a lot of...challenges here. This feels...like a lot of opportunity to make it a win win for both parties involved. I would...offer exactly that—I'll buy it at this purchase price. I'm going to ask for no money down so I can put that cash into deferred maintenance. But then I'm going to pay you at a fixed interest over the next, you know, whatever timeframe you guys agree on...” (08:19)
• Ashley’s Strategy:
  • Read deeper into the family member's trust proposal:
    • “He is willing...to put them into a trust with me as the beneficiary as long as I agree to take over all management responsibilities...So basically he has two options here: buy at a discount now, or inherit them later by managing them.” (09:27)
    • She leans toward the long-term option: “I would put them into a trust. I’d hire third-party management, do asset management, and inherit $2 million in property.” (09:54)
    • Tax advantage: “When you become the beneficiary, your new tax basis is the property’s value at that time, which can mean zero taxes if you sell right away.” (10:40)

Ashley’s Additional Tips:

• If taking the trust route, negotiate to lend funds for repairs from your line of credit, with repayment through the property’s income (possibly with a markup), so you aren’t fronting big cash for decades.
• Caveat:
  • Be clear on your decision-making control during the management phase.
  • Have everything in writing, especially roles, responsibilities, and protocols for needed capital infusions.

Tony & Ashley’s Joint Notes:

• If your goal is to eventually 1031 and scale up, outright purchase may suit you better than trust/inheritance.
• Consult with a trust/legal expert, as nuances in debt handling on trust properties can affect strategy. (They reference the importance of consulting professionals like Brian Bradley, asset protection specialist.)

Memorable Quotes:

• Ashley: “Is making $2 million over 20 years worth it? Plus the properties will…hopefully appreciate even more over the period of time.” (10:01)
• Tony: “If your strategy is to keep it for the rest of your life, then keeping it through a trust might be a better option from both a tax perspective and almost even asset protection perspective.” (13:57)

3. Market Selection for House Hacking and Long-Distance Investment

(21:35–25:45)

• Listener "Jade" (RN; husband entering carpentry) asks where to buy a five- to six-bedroom property for house hacking, debating between renting out their Wisconsin home or moving to (and renting in) California.
• Ashley’s Advice:
  • “I love this! Analyze markets, move to where you get the best opportunity...That is such a cool thing to be able to do to set yourself up financially.” (22:45)
  • Practical point: California is tough from a tax and property pricing standpoint.
• Tony’s Guidance:
  • Ask yourself why a move to California? Is it for job income, family, lifestyle?
  • “If, in either way, you're going to turn the property in Wisconsin to a rental...then it's just okay, well where can we go to actually make the most money and...net at the end of the day have the most money in our pockets?" (23:49)
  • There are 20,000+ U.S. cities—success is about matching your criteria (population growth, low crime, good schools, job diversity), not “finding the one best place.”
    • “I think I would spend less time necessarily worried about the actual city and just more time focused on what are the criteria that we're focused on. And just filtering cities through that to see if they actually match.” (25:20)
  • If Wisconsin fits these criteria and lifestyle, house-hack where you are!

Notable Quotes & Memorable Moments

• Ashley (about timing):
  “Don’t get caught up on not buying just because interest rates are high right now.” (03:49)
• Tony (about trust strategy):
  “If your strategy is to keep it for the rest of your life...then keeping it through a trust might be a better option from both a tax perspective and almost even asset protection perspective.” (13:57)
• Ashley (on living where the deals are):
  “Analyze markets, move to where you get the best opportunity, house hack, and after a year, move back if it doesn’t work out!” (22:45)
• Tony (on investing):
  “There are plenty of cities across the country where it makes sense for you to invest—the goal is just to find the cities that actually match what it is you’re looking for.” (25:17)

Important Timestamps

• 00:26: Q1: Is it worth buying with high current interest rates?
• 04:38: (Ad break skipped)
• 06:42: Q2: Should I buy/take over family property with seller financing or trust?
• 13:57: Inheritance, capital gains, and trust mechanics discussion
• 22:45: Q3: Should we move markets for a house hack? Best markets for large house hacks
• 25:20: Tony’s market selection blueprint

Core Takeaways

• Action beats paralysis: Even in high-interest environments, opportunities exist with careful analysis and negotiation.
• Family & creative deals: Seller financing and trusts can create generational wealth—align structure with your goals, know the tax implications, and get everything in writing.
• Location choice: The “best” market matches your goals and situation, not a universal ranking. Sometimes, staying put is optimal.
• Always clarify your motivations and investment objectives before making major decisions.

If you’re a rookie property investor, this episode provides encouragement and step-by-step logic to navigate major early choices—especially when family, creative financing, and market selection are involved.