Weird that I missed this thread when it was first posted. It's a topic worth some thought -- sometimes you want something, get it, enjoy it for a while and then move on. The New England coast is a beautiful place to sail and live. OP, I'm sure you'll cherish the memories of the local spots you've sailed to, and of course there's always chartering if you get an itch to sail again.
When we first got married we bought a 40' catamaran, sailed and lived aboard full-time for 3 years, then went back to w*rk briefly and sold it a couple years later. It was the right purchase at the time, and we had an amazing experience while we were young & able to do it. However, we knew we wanted to do all sorts of traveling, and when you own a boat or even a vacation home or RV, it often seems like you are "wasting it" if you decide to travel anywhere else. Or at least it seemed that way for us. It was the same when we bought an RV van a few years later -- we had an extended Alaska roadtrip adventure with it, made memories to cherish, then sold it when we were ready for something different. Now we have the time and freedom to travel anywhere and stay as long or as little as we like (within the budget of course). I'm a firm believer that it's okay to do a thing for a while, appreciate it while it lasts, and move on to something else when the time is right. For all the discussions on the forum about withdrawal rates and one more year, what I think ER is really all about is the ability & financial freedom to decide what we get to do every day.