>>1039814It's pretty easy (relatively speaking. Anything on a boat is just a little bit harder and more expensive than ashore) to insulate a boat. Be sure to get a bubble (inflatable plastic dome thing for the cockpit/aft deck area; really helps entry, exit, and helm checks in the snow) and hull agitators if your harbor freezes solid.
Also ask yourself what you honestly plan to do afloat. Not what you think you'll do, what you'll actually do. If you really and truly know for a fact that you'll be sailing at least every weekend go ahead and get a sailboat. If you really and truly just need a place to live that you can take out on the coast from time to time, go for a motor cruiser/trawler/whatever or a power sailer. A sailboat is relatively cheaper to voyage in at the expense of living space, while a motor boat can cost more to move but is usually far more comfortable to live aboard.
Also the "sailboats are cheaper" thing is kind of a myth. Rope and canvas aren't cheap, and turning them into lines and sails is a skill you're going to pay for with either an assload of your personal time or money. Engine work is also expensive, but in my experience is generally easier for the layman to learn than sail making. Sure, wind is free, but the more you use your sails the more often you have to replace them. I'm not trying to talk you out of anything, but having lived full time aboard sail craft and now a trawler, both are only as cheap to operate as you are educated.
Errata:
Get some solar panels or a wind generator, or both. In temperate weather you can easily run all necessary electronics for free, without buying shore power or running your engines.
Clean and paint your own hull, and learn to check and secure your own seals. It's a pain in the ass, but fairly uncomplicated. There's literally no reason not to do it yourself.
In the States anyway, off road or agricultural diesel is cheaper than marine diesel. Buy the ag stuff and carry it back with you.
