Off Market deals approach

Madison, WI · Member since 2024 · 4 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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Kasing Ng

Accountant · San Francisco, CA | Remote · Member since 2026 · 70 posts · 36 votes

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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Kasing Ng
Accountant · San Francisco, CA | Remote · Member since 2026 · 70 posts · 36 votes
9h
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 · 921 votes
9h
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.
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- Yahya RadmanPro Member
  OP
  Madison, WI · Member since 2024 · 4 posts · 1 vote
  8h
  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 · 4 posts · 1 vote
8h
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 · 272 posts · 89 votes
4h
@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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