buying a boat can be such a crap shoot.
I few of the issues we've sorted out.
Comfortable seating in the salon, not just an L shaped bench around the table.
Hull design that gives a relatively "dry" ride. Our Camano does that, our old Bayliner 43 did not.
Good dry windows. dealing with leakers is such a pain.
For us, turns out having the ladder to the flybridge tilted a bit...not vertical...makes all the difference. i.e. can you climb it with one hand.
Ease of service access. I do all my own repair and service and being able to get to things is important.
While not critical, keep in mind that if you have to replace a bunch of electronics, it gets expensive. Having a working autopilot, an uptodate chart plotter and depth finder and radar saves you a few thousand.
Ease of getting on and off. For example, we had an aft cabin boat for a while and it was tougher boarding than cockpit boats.
Diesel power. Personal preference, but I'd not have a large gas boat. Diesels are just easier.
economy. It wasn't THE deal, but going from the bayliner to the camano saves more than half the fuel bill
Figuring out whether you can live with 7-8 knots. That's a huge deal.
there are just so many things. On the one hand, without having spent a lot of time on boats, its hard to know which ones are important to you. On the other hand, like anything else, once you pick one and purchase it, you'll get used to it and like it. Just human nature.
good luck and have fun