Off Market deals approach

Madison, WI · Member since 2024 · 5 posts · 1 vote

Hello everyone.

First time poster and long time fence sitter. I recently bought a SF and have this ball rolling. I am currently attacking a market with my agent and I am seeing some great fits for my buy box. Two opportunities have come my way in a market that is incredibly aggressive. If the properties go on the market, they will be out of my price range and the numbers won't number.

Prop 1: Duplex, 2/1, zestimate is $537k, Income $3k/mo, old man wants to get rid of it but hoping for family to inherit (they aren't interested)

Prop 2: SF, 3/1.5, zestimate is $435k, rent $2.5k/mo, couple split and neither can buy out the other.

How would you approach this? I would love to hear your ideas.

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Arman AhmedPro Member

Real Estate Agent · Columbus Cleveland Dayton, OH · Member since 2024 · 2k+ posts · 923 votes

Quote from @Yahya Radman:

Hello everyone.

Prop 1: Duplex, 2/1, zestimate is $537k, Income $3k/mo, old man wants to get rid of it but hoping for family to inherit (they aren't interested)

Prop 2: SF, 3/1.5, zestimate is $435k, rent $2.5k/mo, couple split and neither can buy out the other.

How would you approach this? I would love to hear your ideas.

If the numbers only work off-market, I’d focus on building a relationship with the owners first instead of trying to force the deal. Find out what they want, their timeline, and what price would actually make sense for both sides. Since you’re already in the Midwest, I’d also keep some neighboring markets on your radar. There are areas with lower entry prices where it’s still possible to find deals that actually cash flow.

[email protected]614-418-6081

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Kasing Ng
Accountant · San Francisco, CA · Member since 2026 · 74 posts · 38 votes
1d
Welcome Yahya, first post and already digging up off market deals, that is the right instinct. I am a CPA, so I will stay out of the offer structure and just flag something that could actually win you these two without paying up.
Both of these sellers probably have a tax reason they are stuck, and that is your opening.
The old man on the duplex has likely owned it forever. If he just sells it outright, a big chunk of that price goes straight to taxes, which is often the real reason someone hangs onto a place they do not even want. If you offer to let him carry the financing and take payments over time instead of one lump sum, he spreads that tax bill out too. A lot of older owners like that a lot more than a cash offer, and it can get you in cheaper than the open market would.
The couple splitting up is the opposite. If one of them still lives there, they can probably walk away with a good chunk of profit tax free right now, but that only lasts so long after they move out. So for them the pressure is to just get it done, and a clean quick close might matter more than the money.
If I were you I would quietly find out how long each one has owned the place and whether they lived in it or rented it out. That one answer tells you which of these two buttons to push. Happy to walk through the tax side of either if you want.
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Arman AhmedPro Member
Real Estate Agent · Columbus Cleveland Dayton, OH · Member since 2024 · 2k+ posts · 923 votes
1d
Quote from @Yahya Radman:
Hello everyone.
First time poster and long time fence sitter. I recently bought a SF and have this ball rolling. I am currently attacking a market with my agent and I am seeing some great fits for my buy box. Two opportunities have come my way in a market that is incredibly aggressive. If the properties go on the market, they will be out of my price range and the numbers won't number.
Prop 1: Duplex, 2/1, zestimate is $537k, Income $3k/mo, old man wants to get rid of it but hoping for family to inherit (they aren't interested)
Prop 2: SF, 3/1.5, zestimate is $435k, rent $2.5k/mo, couple split and neither can buy out the other.
How would you approach this? I would love to hear your ideas.
If the numbers only work off-market, I’d focus on building a relationship with the owners first instead of trying to force the deal. Find out what they want, their timeline, and what price would actually make sense for both sides. Since you’re already in the Midwest, I’d also keep some neighboring markets on your radar. There are areas with lower entry prices where it’s still possible to find deals that actually cash flow.
[email protected]614-418-6081
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- Yahya RadmanPro Member
  OP
  Madison, WI · Member since 2024 · 5 posts · 1 vote
  1d
  Couldn't agree more. These two are in my backyard and had to ask.
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Yahya RadmanPro Member
OP
Madison, WI · Member since 2024 · 5 posts · 1 vote
1d
Amazing. The SF they've been there more than 8 years, never rented. The duplex, his old house so the note is all his, he did complain about the taxes and repairs and the difficulty of renting it to people. I would love to learn how to structure something that would be in his best interest and my gain. I'll do some digging on both.
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Divin KanyamaBusiness Member
Accountant · Seattle, WA · Member since 2025 · 301 posts · 95 votes
1d
@Yahya Radman Both could be worth pursuing, but the Zestimate and current rent are only starting points. First verify actual market value, leases, expenses, condition, title, and the sellers’ timelines, then set a maximum price based on the return you need. For the duplex, the owner may value simplicity, dependable payments, or a structure that supports his family’s goals. For the single-family home, both owners need to agree, so a clean sale or properly documented buyout may matter more than creative terms. Ask open-ended questions, solve the sellers’ real problems, and have an attorney review any seller financing, subject-to, or partnership arrangement. In an aggressive market, clarity and certainty can be more persuasive than simply offering the highest price.
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Ashish AcharyaBusiness Member
CPA, CFP®, PFS · FL · Member since 2017 · 5k+ posts · 3k+ votes
1d
Yahya, I’d approach these two situations a little differently because the seller motivation seems to be the real opportunity.
On the duplex, if the owner wants the property to stay within the family but the family isn’t interested, I’d first understand what he actually wants out of the sale. If the biggest issue is timing, price, or not wanting to deal with a traditional listing, there may be room to structure something that solves his problem without having to compete at the eventual market price.
The second property sounds more like a situation where the ownership structure may be creating the opportunity. If the couple is split and neither can buy the other out, I’d want to understand whether both owners have the same goals around price, timing, and carrying the property. Sometimes the solution is less about getting a huge discount and more about creating a structure that makes it easier for everyone to exit.
Either way, I’d run the numbers before getting too creative. If the property doesn’t work as a rental at a realistic purchase price, creative financing alone doesn’t necessarily fix it. I’d compare the actual rent, expenses, financing, cash required, and return under a few different purchase and financing scenarios.
Feel free to DM me, I’d be happy to send over our Turn Key Rental Analyzer so you can run both properties through the numbers before deciding how aggressively to pursue them.
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Don KonipolBusiness Member
Investor · The Woodlands TX / Avon, CT · Member since 2009 · 6k+ posts · 10k+ votes
1d
Don’t rush in to buy property when you’re inexperienced and lack extensive knowledge - it can prove too costly and sour you on investing.
So, instead learn all you can by reading real estate text books about real estate principles, real estate law, and real estate finance. Engage with the sellers/brokers of properties that interest you. Make offers your comfortable with at offering prices that provide you with an above market ROI, and don't worry if most offers are rejected - you're looking for the few that are willing to sell at a price making it a good deal for you.
Quite frankly, while many of the suggestions, tactics, strategies and tips you receive are good, you’re not at the stage yet where you can profitably use them. Most require a certain level of knowledge and experience to use effectively; right now you want to learn, prepare for a future successful investing career, and limit your downside. Make your offers contingent on a third party (advisor) review, and one way or another find and engage an advisor whose success in real estate and trust makes them qualified to offer advice.
48 years ago as a newbie investor I rushed in just because deals were available to me. I purchased 40 SFR just because I could. And while I had the education and maybe the knowledge, I didn't have the experience. To get out from under these negative cash flow purchases I had to bring money to the closing table to sell them! Fortunately, I had previously done a purchase of an office/warehouse that turned out a big winner, and more than offset my losses on the SFR. The lessons I learned were invaluable, but I wish I had learned the lessons without paying such a high cost.
Go slow, learn real estate principles, finance and law, and gain as much local property knowledge and sector knowledge as;edge as you can. I can tell by your post you’re going to be very successful.
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- Yahya RadmanPro Member
  OP
  Madison, WI · Member since 2024 · 5 posts · 1 vote
  1d
  Thank you Don. I appreciate the insight.
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Dan H.Pro Member
Investor · Poway, CA · Member since 2015 · 7k+ posts · 8k+ votes
15h
Not really answering the question, but related to @Don Konipol reply, what is the envisioned source of return here?
They would need to sell far below zestimate to come close to positive cash flow and based on price the historical appreciation is below national average. Is there a value add component? Are the listed rents far below market rate? Do you expect the properties to appreciate better than they have historically.
Not every off market purchase is a bargain. Do conservative underwriting. Compare the result with the 50% rule. Compare the projected return with other options. Sp500 has historical average of ~10%. More risk for Fab5 or mag 7. Good syndications. Commodities. Notes. The list is nearly endless.
I want my residential RE returns to be much higher than returns projected for passive options.
Good luck
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Kate Sanchez
Member since 2025 · 244 posts · 98 votes
4h
@Yahya Radman Go with the duplex! Multi-family scales better, and motivated sellers with unhelpful family are prime off-market targets. Direct mail or a personal letter works best here!
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