I spent 15 years reading acquisition files from the other side of the desk - first at Wells Fargo, then at PNC, most recently as VP, Relationship Manager. I've watched a lot of good deals die in underwriting for reasons the buyer never saw coming. A few of those reasons show up again and again: 1. Buyers treat debt service and salary as separate hurdles. A lender treats them as one. Coverage gets calculated after a market-rate salary is subtracted. If your plan only works because you're paying yourself less than the job is worth, the lender is going to catch that before you do. 2. Add-backs that live in a spreadsheet and nowhere else. Every add-back gets recast during underwriting, and undocumented ones disappear. That doesn't just move the price down. It moves the loan size down. Buyers are often surprised to learn those are the same number. 3. Working capital nobody priced. Inventory builds, prepaid revenue, a fuel cost spike, a seasonal swing. These create cash needs after closing that never show up in the purchase price, right when the buyer has the least cushion to absorb them. 4. Industry-specific triggers. Environmental assessments on auto repair real estate. Multiemployer pension withdrawal liability on union trades. Licensing ratios in childcare. None of these are secrets, but nobody puts them on a generic diligence checklist. None of this means walk away. Almost always, it means the price was set on a version of the business that doesn't survive the lender's math - and the fix is to reprice or restructure, not to panic. I do this kind of financial review independently now - recasting earnings, testing coverage, and telling a buyer honestly whether a deal clears before they spend real money finding out the hard way. Happy to answer questions in the comments or via DM.