I'm looking at a commercial services business where the owner is the relationship. He sold most of the accounts, he's the name customers call, and the repeat work flows through him personally. Revenue and margins look solid. The obvious risk is that the relationships walk out the door with him. My working thesis: with a long enough transition and a deliberate handoff, most of that is transferable. Customers care about the work getting done well more than they care about whose truck shows up. But I'd rather stress test that assumption than find out at month four. More context: Competitive deal. Offer is submitted (not yet under LOI), including a 10% forgiveable seller note. DSCR year 1 is 2.34 so there is room for the risk of customer loss. Meeting sellers tomorrow. For those who have bought a business like this or have experience with this matter: - What specific questions should I ask the owner to tease out vulnerabilities? - What did the handoff actually look like? Joint visits, warm intros, seller staying on payroll? What worked and what was theater? - How long is long enough? I hear 90 days as the standard and 6 to 12 months as the safer answer. Where did you land, and would you do it differently? - What did you actually lose? Real attrition numbers in year one, and how much of it was relationship driven versus price, service, or normal churn. - What structure protected you? What would you insist on now? - What's the tell that relationships aren't transferable at all? The signal that made you walk instead of structure around it. Appreciate any perspective here!