Well, that's a pretty open ended question. As for costs, the ballpark estimate I've heard for
maintenance is 10% of
purchase price per year. I've spent about that, although you would probably spend less if you bought a newer
boat. I have a 38'
LOA powerboat and I spend about $10k per year for dockage (summer dockage and
winter haulout). I burn about 35 gallons of
fuel per hour cruising around the
Long Island Sound. Dockage in overnight
ports is about $100 per night. I have an older boat, so I've spent a whole lot of
money upgrading and customizing it, in addition to the costs I've mentioned. I live near the boat, so I have done a fair bit of the
work myself.
Mechanic rates are about $100/hr for the stuff I don't want to do. I get my
Caribbean fix by chartering a cat every
winter for a week. Figure about $10k for that, although you could do it for a whole lot less.
So as for your option 1, I would suggest getting the smallest boat you can comfortably spend a week on. Get something new enough such that you won't have to replace a bunch of stuff, or old enough such that it has already been overhauled. Make sure it is a popular boat so you can resell it as you better define your needs. Don't forget the
learning curve you will face will be pretty daunting. Once you get into the size of vessel you can spend a week on, you really need to be a pretty good seaman.
Brett