I know for a fact that I would not have what it takes to live in C.R.
As the dollar declines, my investments continue to be worth less, making a fat retirement a lot less likely. But more than that, if one gets past the chicas, ocean breezes and fresh fruit...what does C.R. really have to offfer? The infrastructure from what I've seen really sucks. You can tell a lot about a nation by looking at the condition of its public works; bridges, roadways, airport, sidewalks. Frankly, C.R. doesn't invest well in itself, and I refuse to believe it's simply a matter of poverty.
Secondly, tico attitude and behavior has been thoroughly discussed elsewhere here, and I don't think I could deal with the "cosas muy ticas" and petty theft for very long without becoming disenchanted.
Finally, only a small percentage of us speak Spanish with complete fluency, and those are the guys who either grew up speaking Spanish or who have worked as professional translators/linguists. Even I with my very decent Spanish would eventually run headlong into linguistic brick walls. This is not only frustrating, but depending upon the circumstances could be life-threatening.
I hope that anyone thinking seriously of retiring to or working in Costa Rica really does his homework with as much dilligence as he can. This move is not something to be taken lightly, and if all you're moving for is access to hot chicas half your age, you're stupid IMHO.