Many boats are fine for beginners . . . not too big, not too powerful, not too complicated.
Have you taken water safety/boating safety courses? You should.
How much money is a lot?
Use the buyers checklist that JB posted.
Engine/outdrive - OMC sterndrive engines are a concern (OMC went out of business over 20 years ago). Ford-based engines are a concern (Ford got out of the marine engine thing, leaving it to GM)
How good are you with a socket wrench? Older boats will always need some wrenching. Newer ones are not much better in some cases.
Welcome to iBoats and welcome to boating. Got any boat-a-holic friends that can guide you first hand?