Diligence is mostly an exercise in pricing problems, not avoiding them. A leaky roof, a tired website, a payroll that is two people too heavy: these are line items you negotiate against and fix after close. The danger is treating every problem that way, because a handful of them do not respond to price at all. They are structural, they travel with the business through the ownership change, and the discount you win at the table never compensates for the risk you inherit. This piece is about those five.
The difference between a discount and a trap
Every seller's business has flaws, and a good buyer is glad to find them, because each one is a reason to pay less. That is the normal grammar of a deal: you uncover a weakness, you assign it a cost, and you subtract that cost from the price. Deferred maintenance, an underpriced book of work, a manager who is coasting toward retirement, these are problems you can see, size, and solve with money and time after you own the place.