One thing I always looked at was the registration, is it current or did it expire some years ago. Around here we have guys that actually use their boats and then we we have those guys that use them as yard decoration.
About 10 years while taking shortcut home from work I spotted what looked like a Catalina 22 sailboat in a side yard, it had a cover on it that was faded and starting to shred. I knocked on the door and asked if it was for sale and was told very bluntly, NO IT IS NOT FOR SALE, well here it is 10 years later and there it still sits the cover is shredded and the boat is covered in vine, Go Figure some people.
Yes you gotta take a good hard look and make the seller start it up, but before he does pull the hood and feel the engine to see if it is warm. Some guys with a hard to start motor will get it warmed up and running before you show up. when it starts and runs check all the gauges to see if they are working, Tach, temp and volts are what you are looking for and if power tilt see if there is a gauge for that and if it works, these are expensive to fix items, that big a motor might also have a water pressure gauge