Aesthetics and practical issues ultimately dictate what
boat you choose. Where will you keep it? Will you
live aboard? Do you want to enjoy the
water and return to
dock or
mooring, or do you want to travel? Those are practical issues. Do you like the quiet of a sailboat, or the speed of a
power boat? Those are the aesthetic questions.
Aside from that, if you choose to sail, it might be a good idea to start sailing some smaller
boats first, and
crewing on other
boats. Smaller boats will help you understand how
sails work, and are quicker to respond.
Crewing or sailing on other people's boats gives you a sense of what style
boat really feels right. Volume of a solid increases with the cube of a side, and cost of boats similarly goes up exponentially with size.