Dont do a pontoon, they are super boring and you might as well just sit on a dock all day.
I have been around boats my whole life and love being on the water. I am currently in the market for a ~20-21 ft ski boat with direct drive. My budget is 20-30k and I have already found some great options. For me its all about what you can do behind the boat thats important, and then relaxing and comfort on the boat. I want something I can slalom ski behind, surf, wakeboard. To surf you need a boat with either direct drive or V drive. Do you plan on doing any activities behind the boat? You won't be able to do much with 40hp. You could pick up a good used boat with stern drive or outboard which would be a good platform for chilling on the water but you can still ski/board/tube behind it. Whats your budget?
_____ASP______
current ski quiver:
park, all mtn 181 ON3P Kartel 98
park,all mtn: 181 Armada AR7
big mtn, pow: 185 Armada JJ