Interesting post as I am also contemplating planning/options for retirement (about 13-15 yrs away given my kid’s ages). The US is the only developed country where a large part of its citizens struggle to retire at the typical age (65ish) and maintain the same lifestyle.
Most intriguing is that in today’s finance news the frequent articles that pop up are “Top 10 retirement outside of the US”. I believe it is a soft attempt to prepare the nearly retirement age crowd that in the US the majority won’t make it w/out strong retirement planning. The finance news media provides plan B for you if you didn’t save. Hence, countries like Cost Rica, Mexico, Thailand, take your Eastern EU pick are always options to consider. I am a transplant too (23 yrs in San Diego and with the first 20 yrs in Eastern EU somewhere). Our US reality of social pension + medical cost/support will most likely drive me out of the US. It isn’t for the lack of planning, but the desire to retire earlier (around 55-57).
Long ago, another transplant friend properly noted that all you need to be successful in the US, are 2 things: #1 a good work uniform, and #2 a good pajama (to be read as: work + sleep & repeat). It also tells you a bit about our society where standard/average productive people that aren’t productive anymore (retired) would be better in another country or nicely pushed away.
I travel regularly, and Europe has its charm. Eastern EU is pretty cheap and fun, but the cold winters push me away. It might be a formula that Summers in Europe and Winters in (Mexico, Costa Rica, Thailand)…… I prefer tropical climate & good fishing nearby, however the wifey likes home (Eastern EU) because of the paid off real estate/social atmosphere/people/lifestyle etc.
P.S. Also interesting that most of my vacations are now planned around places I would consider retiring for winter (Mexico, Thailand are lovely -checked off my list and Costa Rica will be checked off in a few months).