747Pilot
So let me get this straight you are actually thinking of a "not quite retired Pilots resthome"
Sounds pretty good actually! Could certainly customize the services offered.
To give you an idea about COL and the effects of no direct taxes, (property tax is a one-time charge on purchase)
A Canadian friend of mine came here, built his own home (self contracted, hired sub-contractors) it is now valued at US$ 750K, He said that had he purchased the house while remaining and working in Canada, he would have had to earn 2 million in order to have sufficient money (after tax) to buy the house and it obviously didn't cost him the full value to build it.
my estimate of grocery cost for a small family eating well but not buying everything pre-cooked, would be in the region of US 200 +/- 15% per week, booze and cigarettes would come on top of that. It is generally thought that the breakeven income for a family of four is around CI$ 30k per annum. CI$ 1.00 = US$ 1.25