Would You Buy This Deal Again?

Question

Here’s a question I think investors should ask themselves more often:

If you knew everything you know now, would you still buy the property?

Not because the project went perfectly.

Not because it made money.

But because the original assumptions, risks, and strategy still made sense with what you know today.

That answer can reveal a lot about how we actually make investment decisions.

What experience has changed the way you evaluate your next deal?

Divin Kanyama · Answer

@Siahna Im I like the distinction between a good outcome and a good decision. I’d want to separate what I reasonably couldn’t have known from what I could have verified but didn’t. A deal working out wouldn’t excuse skipping that homework, just as an unexpected setback wouldn’t automatically make the original decision wrong.

The part I’d carry into the next deal is being clearer about which assumptions I’ve verified and which ones I’m simply hoping will hold. I’d also put my time and cash reserves into the analysis—not just the projected return. If the plan only works with a smooth rehab, immediate rent increases, and an easy refinance, I’d want to rethink it before buying. For me, the useful lesson wouldn’t just be “would I buy it again,” but what I’d need to verify or change before saying yes.

Matthew Morrow · Answer

@Siahna Im for me it comes down to purchase price. If I paid a number that still left room when the rehab ran over, I'd buy it again. The ones I wouldn't are the ones where I told myself the numbers worked when they only worked if nothing went wrong. Deferred capex is where I got burned. Now I assume the last owner didn't maintain it the way I would, that there's something behind the walls, and I show up with reserves for the big items. That changed how I underwrite more than any single deal result.

Anthony Smith · Answer

Detroit taught me this the expensive way. Three things I underwrite completely differently now:

1. Taxes at the post-sale number. In Michigan the taxable value uncaps after a sale, so the seller's tax bill is fiction. I run every deal at the uncapped estimate — it has killed more 'deals' than any other line.

2. Insurance quoted before the offer, not after. Carrier appetite for older Detroit rentals is its own underwriting step, and the quote can be double the guess.

3. Security and sequencing on vacant houses. I had a brand-new furnace and water heater stolen out of a vacant flip. Now mechanicals go in as late as possible, and install timing is part of the budget, not an afterthought.

Would I buy my early Detroit houses again at the prices I paid? A couple of them, no — not because they lost money, but because the assumptions were luck, not analysis. The deals I would buy again are the ones where the numbers still worked after I replaced every optimistic assumption with a verified one.

Jeremy White · Answer

A habit that helps is writing down your assumptions for rent, repairs, vacancy and exit before you close, then comparing them with what actually happened after the first year. The gaps usually show which numbers were too optimistic, and those are the ones to stress test harder on the next deal. Keeping the notes in one place makes the review quick.

Siahna Im · Answer

I really like how you separated the outcome from the decision itself. A profitable deal doesn't always mean every decision was right, and a difficult project doesn't necessarily mean the original analysis was poor. Being honest about what was verified versus what was assumed is such an important part of improving as an investor. Has that changed the way you approach due diligence on new deals?

Siahna Im · Answer

I agree that having enough room in the purchase price is key. A deal can look great on paper, but deferred maintenance and unexpected repairs can quickly change the numbers. Building in reserves and planning for the worst-case scenario seem like habits that can save investors a lot of stress. Which major repair do you now make sure to account for first?

Siahna Im · Answer

That Detroit experience is a good reminder that the purchase price is only one piece of the puzzle. Taxes, insurance, and even the timing of installing equipment can make a huge difference. The stolen furnace and water heater are tough lessons! Have you found that these precautions have made your recent projects more predictable?

Siahna Im · Answer

That’s a great point. Reviewing your original assumptions against what actually happened can reveal so much, especially when it comes to expenses and vacancy. I think a lot of investors learn more from those gaps than from the deal’s final profit. Do you usually review your numbers after the first year, or after every completed project?

Would You Buy This Deal Again?

Would You Buy This Deal Again?

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