How do you sanity-check numbers before locking up a wholesale deal?

Question

I've seen a lot of deals fall apart because of early assumptions were too aggressive so I've been tightening up my front end screening

what usually kills a wholesale deal early for you?

Robert Street · Answer

@Ken M.

That makes a lot of sense.

I’ve found that focusing on whether the buyer relationship actually works — instead of forcing a deal to fit — saves a ton of time and friction on the front end.

When expectations and flexibility line up, it’s usually straightforward to make everyone whole. And when they don’t, walking away clean almost always beats dragging something out that was never really aligned to begin with.

Robert Street · Answer

@Ken M.

That makes sense — that’s actually a smart way to eliminate a lot of the failure points I mentioned.

When you assume worst-case condition, avoid bank leverage, and structure creatively, ARV compression and contractor risk matter a lot less because you’re not dependent on a perfect resale window...................  On my side, even when wholesaling, I’ve been trying to adopt more of that same mindset on the front end — underwriting deals as if they won’t be pretty, assuming heavier rehab, and padding for holding/tax exposure so the deal survives even if it doesn’t go exactly to plan.

Out of curiosity, when you’re buying creatively, what usually becomes the deciding factor for you early on — price control, seller motivation, or deal structure flexibility?

Robert Street · Answer

@Ken M.

Agreed ....... that list pretty much covers where most deals get hurt. What I’ve been noticing is that a lot of those issues show up because the front-end assumptions are too narrow. ARV guesswork and missed costs usually compound once contractor performance, mechanical age, or holding/tax exposure enter the picture.That’s why I’ve been leaning more toward ranges and worst-case padding early, especially on roofing, HVAC, and systems where age alone can blow a budget. It doesn’t eliminate risk, but it makes surprises less fatal.

Out of curiosity, which of those has burned you the most historically  rehab overruns or ARV compression?