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?

Henry Lazerow · Answer

I would 10x the deals I did if could go back in time lol atleast in Chicago property has gone up a ton. $100k 2 unit in 2013 was $300k in 2019 now is $500 to 600k. Even the flip I did that went over budget by a good 25% still made nice profit as I just held it a year and half ended up six figure net still. As long as buy right with positive cashflow where can hold as long as need to and are in an appreciating market, scale is the winner. The small extra negotiations or getting a slightly better buy in price means nothing versus long term compounding appreciation.

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.

Jarret Jarvis · Answer

Great question. I've started asking it about my own deals, and it changes how you look at them.

For me the honest answer is usually yes, I'd still buy, but not at the same price or with the same plan. Most of what I'd do differently has nothing to do with the property. It's how I underwrote it. The biggest change for me is that I don't underwrite the best-case version of a deal anymore. Early on I'd plug in today's taxes, today's insurance, and a rent number that assumed everything went right. Now I start with what could go wrong. Where do taxes go after the next reassessment? What happens if a unit sits empty for two months? What if the roof or the boiler goes in year one? If the deal only works when everything goes right, I pass. Owning a short-term rental changed my thinking too. A great summer can make you think you're a genius. Then you live through the slow months and realize you have to plan around the whole year, not your best weekends.

The other big one is reserves. I used to think of reserves as money sitting around doing nothing. Now I think of them as the thing that lets you hold a property through a bad stretch instead of being forced to sell at the wrong time. So my filter now is simple. Would I still want this property if it performed like an average deal instead of a great one? If the answer is yes, I'm in.

Alex S. · Answer

Was it a sound buy, or did it only work because prices went up? I'd rerun the original purchase numbers with what I now know about repairs and vacancy, plus the time it actually takes to manage.

Henry Lazerow · Answer

I think there is still a ton of upside in the nice Chicago areas that are gentrifying like Rogers Park, Albany Park, Avondale, bronzeville, etc. rents in these areas are increasing 5% to 10% a year right now with single family builds hitting new highs as more and more higher income people move in. Some of the lower credit and higher crime areas of the city though have prices high for no viable reason that I see atleast and I think those areas are way overpriced for what they are.

Siahna Im · Answer

That's a great point. Sometimes looking back, the bigger opportunity wasn't just making a good deal but having the confidence to scale when the market and numbers made sense. Appreciation can make a huge difference over time, especially when you buy right and have room to hold. Curious, do you think today's Chicago market still offers similar opportunities for investors?

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?

Would You Buy This Deal Again?

Would You Buy This Deal Again?

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