Some small-house love:

[Starboard Tack]

17. Your idea might be crazy, but I like your attitude and imagination.

I am pretty much doing what you describe, except on water rather than in the air. I find water to be a more friendly medium than either land or air, especially in California or any area with major seismic activity.
In terms of cost, I find living on the water far cheaper than living on land. I have friends who make their own moorings for next to nothing. Some lease moorings in very protected waters. We take moorings in the winter at times, because the rates are very low, about $300/month for us.
I notice you want to live in the Catskills. I had the same dream about 30 years ago and bought a 3+ acre parcel of lakefront property for $15k (doubt it would cost so little these days). Anyway, I was going to build a self sufficient home up there. Never happened, divorce etc.. So we sold it and I moved to southern California, where I'm still loving every minute of it. Lakes and rivers are OK, but I'll take the ocean any day.
We are currently anchored in 12 feet of water behind a protective reef in a small island cove (big enough for 4-5 boats). We spend a fair amount of time here (6-8 weeks a year). There is one other boat here which sailed in yesterday. Sandy beach, palm trees, no people. It even rained last night, all night, which is extremely unusual out here between May and October, but most welcome.