Just to get things started here's some of my conclusions so far -- right or wrong (I have never owned a boat which is why I am asking):
1) Watermakers are high maintenance items
2) Saildrive versus shaft drive is equivocal, but easy engine access is a big plus
3) Epoxy is more durable than vinylester which is more durable than polyester.
4) Solid fiberglass below waterline is lower maintenance particularly on older boats than cored fiberglass
5) Teak decks -- or any exterior wood -- is a huge maintenance item
6) Wood cabin soles are high maintenance
1. Yes and add air-conditioning
2. Sail-drive is more exposed. I get the feeling the sail-drive is easy to install and appeals to racers. It is not a 30 year solution.
3. Yes but Epoxy has to be wetted out just right and cured properly. Lots of ways to screw it up. polyester is still going strong 30 years later.
4. Maybe but what exactly do you mean by maintenance. If you crack it, fix it. If it's cored it's solid, lighter, stiffer etc. and no-one screwed with it whats wrong.
5. Well yea but it looks nice do you want a boat or a clorox bottle. You pick.
6. Again, sure but they look great and compared to the rest of everything that is the least of your worries.