I start by looking at the exhaust and seeing how much residue and what color it is, that tells me how the engine gets run, then I look at the hours and how many between annuals, that tells me how often it gets run and how much it's been run (and sat). That's baseline information to work off of to give me an idea (depending on the model of engine) of what kind of maintenance issues I can expect. It's a multi variable equation with a large fudge factor, you're basically making odds, nothing solid. A nearly new engine could fail on the way home, a past TBO engine could go another 2000. Different components have different issues as well even between brands of the same thing.