In this day of rising land costs and sinking boat values, I can't help but see some larger boats, such as this motorsailer(link below), as a form of suitable housing(I'm a design builder and find smaller dwellings the most interesting). Your trawler makes the best sense in achieving best living space that is also seagoing(or at the least very capable on the coast). Big motorsailers are just another pool of these potential dwellings out there(many are for sale).

For the land dweller along the northeast coast, either renting or owning, if you can see the water, you'll be paying a real premium in rent or housing costs, taxes, utilities, and the enormous "misc" that includes everything from cars to lawn mowers. Add to that the energy costs (figured in the high rent if you don't own) of the expensive north east area, and you could come up with a "living cost factor" that would support an entire lifestyle, with perhaps something left over, if,..., you moved onboard.

For me housing has many parameters that I'd want to meet or come close to(I've lived in many dwellings that I designed). They're not over the top in size or ammenities but they are what make living pleasurable. There's boats and sailing on the one hand(the one I have is more than ample), and then there's housing on the other(the one I live in now has what makes me comfortable).

This motorsailer doesn't meet all those living parameters(but I think it's a workable seasonal dwelling for 2 in the right situation), so I look at the financial benefits.

Scroll down to 60' feet, the Alden motorsailer, SORCERESS. The asking price(far from what it will sell for I imagine) is coming down. First, I'd find out if it's due for the inevitable hull rebuild, and pass if it was. Next, I'd figure in the cost of having a new teak deck built(thinking like I do with housing, no leaks) Put a cap of say 200k for a problem free structure for initial investment. Figure then annual maintenance fees, replacement parts, fuel, dockage/moorage. The big plus is the motorsailer can travel the coast quite affordably.

Then apply the SORCERESS annual figure against the annual Northeast coastal living factor, and see what the bottom line is. If what was left over supported say traveling abroad for half the year, it might be an opportunity for some.