Update on our thoughts....
So after weighing various pro/cons scenarios... we're looking towards buying a completed (or almost completed, more on that later) house as a second home. One that we could use as a BOL and vacation home for a few years.
Given that it would be more of a traditional home than a cabin, it likely would not be paid for 100%, we'd float a small mortgage (50-70k at most). This will allow us to make it what we want it without sacrificing city income during the transition, and we could continue to leverage our city incomes for until we are completely comfortable. The mortgage payment being nothing more than a rounding error in our budget, and be a destination for funds other than savings. (maybe a little QE3 fear here I admit)
Once we are completely comfortable, I alone will seek a job in the area as part of the transition (it looks like high level IT is in strong demand up there, particularly where my salary reqs would be substantially lower). The wife's time will be spent towards growing a market gardening income until such time I can leave IT work and contribute.
Buying land and building doesn't seem to be cost effective, as there seems to be a cash advantage in buying something that needs work. There are a few deals on unfinished houses that work out to just buying land and getting a septic and well installed... with most of the house done. I could basically hire out a handy man for a month to finish things up in a few cases and save 30 grand by my estimations.
Day zero of a purchase would likely include landscape work, including cutting/stumping and planting a personal+ orchard. After the house is mostly livable, we'd consider buying a few sleds both for personal recreation, but as tertiary income via rentals (close to personal degrees of separation, not to the public). I do want at least one sled personally and for snow travel, and an ATV (
http://www.theplotmaster.com/) as a poor man's tractor.
