We have been self employed (and paid for our own insurance) for the last 20 years.
Have you priced health insurance? We just turned 65 but we were paying over $20,000 per year with a high deductible.
If I could be blunt, you can’t afford it. Next time the economy takes a dump (and it will), pick up work will be hard to find.
Save up a lot more. Maybe try living in a used travel trailer or rent a park model in an RV park to expose yourself to other people full timing, while keeping your jobs.
Maybe take classes and find careers that pay decent and let you move around.
Itinerant nursing comes to mind. I have talked to several. They work in Maine or the like for the summer. Take a month or so off then work south in the winter.
Another guy was a Marine diesel guy and followed the boats up and down the Intracoastal year round in a nice fifth wheel.
Pipeline work.
Good luck.
