Are there any boat owners here?

I've never owned a boat. In the near future I might be moving to the American Northeast (either Pennsylvania or Maine) and considering getting one.

Would I want to get a slot at a marina or just build a boatshed on my property and truck it to a waterfront on a trailer? How big of a boat could one reasonably trailer around? Here is the midwest a lot of people own pontoon boats for lakes and keep them at home, but I was thinking of more of a sailboat/small yacht.

Would a boat suitable for the great lakes also be suitable for the ocean, maybe if I wanted to sail down to Gulf for a summer? If I wanted to be able to sail from America Europe (I think it would be a neat journey, I have a friend in Finland I could visit maybe) what kind of craft would I need to make that journey?