Probably enough to dine out in Maine, regularly(we need that).
I envy you on a low stress schedule, moving up the NE coast in June and July, immersed in the optimum climate. Few people take advantage of that, in fact, Snowbirds are most often, a month or more off.
You'll enjoy the best weather, NY, RI, Mass. NH, Maine have to offer the visiting sailor, you can sail to your hearts content-or not move at all; plus, you'll avoid the ticking fall clock,....tic tic tic--gotta do 60nm today---tic tic tic---South-south-south.
Forget breakdowns next fall, your boat will be in suspended animation, safely pickled-in storage. In your suitcase, carry a couple pair of shorts and your Visa card. Explore.
If the life afloat appeals to you, and you want to take the boat south next year, you both - and the boat - will be much better equipped to do so.
I'm very interested in your experience, it's different than the norm and makes a lot of sense to me.
I'll give you my budget estimates, after I've seen a few others....