Welcome to iboats.
How many people aboard will be determining factor on size of boat, along with your tow vehicles capacity and your storage area limitations.
Looking to buy new or used?
Condition is much more important than model year.
No problem getting a 25 year old boat if the hull and engine are in great condition.
I would suggest used for a first boat.
Boats take a huge hit in depreciation the first 2 years, worse than a car.
18-20' long.
Aluminum hull, much less forgiving when learning to handle it, bumping docks and such.
Also aluminum means lighter, so towing won't require a huge truck.
Lighter also means less HP needed, so it can save you $$.
Preferably and outboard model.
Since you will be doing the sports stuff, make fir the motor is at or near the max allowed for the particular boat.
Alumacraft, Lund, Starcraft, Crestliner, Sylvan, and even Tracker all make boats that will fit the need.
If you go with a deck boat, then it will be glass.
Something like this for $9000 would be a great boat to get some experience on.
https://fingerlakes.craigslist.org/b...904170287.html