That is hard. I think if I were in your shoes I would just keep on keeping on in the current job and figure out a part-time/2nd job just to make X dollars to relocate. I'd call it my "relocation project" and do a timeline and figure out how much money you'd like to get off the island and somewhere less expensive where you could live on Social Security.

I'm 64 also, will be 65 this year and am studying to get my State insurance license so I can help my stepson, a broker. You might look into something like that or real estate (if you got a license you would be extremely helpful in any office, even if you did not want to sell product; offices are always needed for phone answerers, etc. and knowing what you are talking about and being licensed to do so would put you ahead of the younger crowd who are not licensed but just want a desk job. I know my stepson uses "housewives" to come and sit/answer the phone when he has to be out of the office but he's having a heck of a time getting real employees as they have to be licensed as he hires someone and they flunk the exam, hence me who we're going to have pass the exam (I find it is hard to learn the stuff though, I won't lie, it's extremely detailed, dry, and confusing :-) so then I can do "special projects" for him (live too far from the office to be much help sitting in to answer phones or file, etc.

But I know my son has a guy who use to have a license many years ago/in a different lifetime studying for one again to help him who's in his 70's, not great health, etc. Old people have to buy insurance, real estate, financial products (CFP) too so age is not a "surprise" or something that might put customers off?