Moving to PR

The climate is great here- summers not really hot and winter temperatures in the seventies are great, right?
The cost of living is not really lower than in the lower 48 though. Next to that, but I'm sure  your read that before, Spanish is the main language here. You can get along with English but it would absolutely be good to be able to speak Spanish.
I don't know what kind of activities you would like; there are wonderful beaches all around, if golf is your thing there are quite a few courses (and from what I hear they are good - I don't play myself). So what are activities you're looking for?

The cost of living here is not cheap. It's comparable to DC in most respects. Dining out is quite expensive. Groceries are expensive. Energy costs are high. Renting or buying can be very expensive if you want a decent place. I'd strongly recommend another location. I lived in Panama for several years and the cost of living there was much better. Panamanians are generally very friendly and Spanish is easier to learn there because their accent is not very strong and not many people speak English. I understand Panama has a relatively easy path to residency if you are older than a certain age (I want to say 45, but I am not 100% sure) and can show a steady income, which you can. The province of Chiriqui, which borders Costa Rica, has a healthy North American community and is not nearly as swelteringly hot as Panama City.

Since living in the PR island is not "cheap" I guess I'll continue to search elsewhere for a retirement place. I am looking into Malaysia, the Philippines and a few other places.

Before you give up, ( No free advertising, Please). There are plenty of inexpensive, livable places in the small towns renting for under $500.

BTW, I learned to fly in an Alon Aircoupe.

Suerte,
Rich