whatever you end up doing is up to you but like everyone said do not buy a new boat. Talking to salesman now they will try and give you the good old “buy now in the off season will prices are down” line but the fact is boating sales are hurting and a deal can be found anytime of the season. Buy a older used boat now and see how you like it and then decided what you want to do. As JayS said you might go in thinking you want to do waterports but then you wished you had a bigger boat for vacation trips or whatever. Growing up we started on a 17 foot sea ray and then moved up to a 22 foot sea Ray cuddy cabin. Now with me getting a boat I know what I want and what size I want but you might decided with something different. Boating is totally different to everyone. some like speed (Like me), some might want comfort, some might want a ski boat. Look into something with a open bow to start with since that will be the most “logical” first boat and move on from there. I also recommend one with a Mercruiser in it and not a Volva Penta.