I made the move some 21 years ago when my carrier in the US went into financial problems and asked for voluntary leave. Having a business that paid the my bills allowed me to take that voluntary leave.
Six months after that began a new adventure in m career as an expat. During the past 21 years as an expat, I've been very lucky and have enjoyed every carrier that I had flown with. I have and continue to experience life abroad I would have never had I returned to the white bread US carrier.
When my contract was up, I either upped for another tour of duty or moved on to a new adventure. IMHO New adventures reduce the chances of the old burn out syndrome. Yeah, there are hoops to jump though but in the long run the experience outweighs the inconveniences that some countries put expats through.
I do see many unhappy crew dogs roaming terminals round the world, especially when I return to the US, with that burnout expression look on their faces. I understand why... trying to jump seat home to be with their families for 2 or 3 days, and back out on the road. That worried look on their faces wondering if they are going to have heated discussions with their spouses because they are never home and living the life of Riley.
I have another four years to go and will be ready to hang up the goggles. Ever since I entered the industry my plan has been to call it quits at age 60, even though the retirement age has been raised to 65. Our plan is to travel around the US in a motor home with a little Honda in tow. I've crisscrossed the US many times in the Flight Levels but never really saw the US. Well now's our chance. There is one thing I don't want to do unless out of absolute necessity, is to travel anyplace by airline.
As for retirement and medical... well, I budgeted for both since the 1970's. Knock wood, my retirement accounts were not affected by the market debacles after 9/11 nor 2008.