Welcome aboard! We also live in upstate NY (in the Catskills) and we opted for a big trailer-sailer. That way we can cruise Maine
for a week, then come home. Cruise Cape Cod
for a week, come home. That's the sort of thing we can fit into our lives right now, what with our work and the kids' school
. We have taken it all up and down the east coast
, and once to Miami
by trailer, then sailed to the Bahamas
If you opt for a non-trailerable boat, you'll just have to choose where to leave it, and what areas will be within your normal cruising radius.
Basically, it's all good. You've made the big decision -- to spend more time on the water. Everything after that is just refinement. Good luck!