A couple of points to consider
#1 a one year "boat club" is a great way to try before you buy - you know get your feet wet
#2 Size matters - Dockage is by the foot. Bottom jobs are by the foot. Dive services are by the foot. The feet and $$ start adding up
#3 Size matters - as in start small - then move up. Driving a 19ft bow rider is a whole lot different than a 28 foot sport fisherman.
#4 Boats are not economical - efficient boats get 2-3 miles per gallon. Seriously. A 30 foot boat gets 1 mile per gallon (avg) a 35 foot boat - gets .5-.8 maybe a gallon per mile if it's a diesel
#5 Diesel mechanics make more per hour
#6 Boat depreciation curves are quite a bit like car depreciation curves. Try and buy one towards the bottom - and you can own a boat for relatively small money. Stay with the classics - or the boats with the higher perceived value and you can typically sell it for what you buy it for (One of the reasons why I have a B28)
I always tell people that owning a boat can make Porsche ownership seem downright cheap.
For the record - my pocket cruiser...