Formal instruction does have its advantages. I took formal sailing lessons, even though I've been sailing for over 20 years, just before I bought my boat, as a refresher. I think it was money well spent.
Joining a sailing club or crewing for someone is also a good stepping stone to owning a boat.
It will probably take you at least six months to outfit a boat for long-term cruising. You really need to learn the systems on the boat inside out, and as you learn about the boat, you will find that there are things you want to change for long-term use.
I sail out of Buzzards Bay, and if you're interested in crewing, let me know via PM.
to Keelhaulin- He does say that he lives on Cape Cod... so that would probably be a good indicator of where he will be sailing initially.