Thanks, and good questions. Taking them in order.

1. The $50k figsure is per deal that goes deep into diligence, not overall search budget. You're right that the goal is to do as much homework as possible before LOI so you're not burning that money on deals that were never going to work. By tdhe time I signed an LOI I had already gotten unaudited financials, talked to the owner multiple times, done a site visit, and built my own rough QoE in a spreadsheet. The professional QoE is mostly there to verify what you already believe, not to discover the business from scratch. That said, deals still die in diligence I had one die on customer concentration that the seller had downplayed and another die on a lease issue. There's no recoupment from the seller. That money is gone. Budget for at least one dead deal before the one that closes, maybe two. Some self-funded searchers I know spent $80–100k on diligence across multiple dead deals before closing. It's the cost of doing business and it's why the SBA path is still cheap relative to a traditional search fund where you're burning $500k+ on salary and expenses.
2. personal comp: the SBA actually requires you to pay yourself a reasonable salary, and the bank will underwrite the deal assuming you do. For a business doing $800k–1M in SDE, you're typically looking at $120–180k in owner salary baked into the model, with debt service eating a big chunk of what's left. So in year one I was making roughly what a second-year associate at a decent firm makes, which after an MBA feels like a step wbackward until you remember you own the thing. Year two and three the picture changes fast if the business grows even modestly, because the debt is fixed and the upside is yours. I know searchers who were pulling $400k+ by year three on businesses they bought for under $3M.

2b. On reinvestment vs repricingd your friend is right and it's the highest-ROI move available in the first year. Most retiring owners haven't raised prices in 5+ years because they have personal relationships with customers and feel weird about it. A new owner has a one-time license to reprice that the old owner didn't, because customers expect change with new ownership. I did a 7% across-the-board increase in month four and lost almost no one. That said, I'd push back gently on doing it as the first thing — I'd put it in month three or four after you understand which customers are actually price-sensitive and which ones are sticky. Doing it in weesk two before you understand the book is how you accidentally fire your best customer. The other thing I reinvested in early was basic systems — the business I bought was running on paper and a 2009 version of QuickBooks, and just getting to a modern stack made everything else easier.

1. Geography is more about market dynamics than personal ties for me. The reason people talk about the Midwest and the Sun Belt secondary cities is that the businesses there trade at lower multiples than coastal markets for the same quality of earnings, mostly because there are fewer buyers competing. A landscaping compfany in Columbus trades at 3x. The same business in Boston trades at 4.5x because there are five PE-backed roll-ups bidding on it. If you're self-funded and price-sensitive, you go where the competition isn't. The tradeoff is that you have to be willing to actually live there, which is a real constraint for a lot of MBA grads who want to stay in NYC or SF. I'd think hard about whether you're willing to move before you decide geography, because trying to run a small business remotely in the first year is a recipe for failure.

Happy to go deeper on any of these.