Central America.
I am pretty much living in Costa Rica. It is a fantastic country. It has gotten a little expensive, but there are still many inexpensive places . It just depends on how close to the beach and amenities you want. Once you have your housing and tansportstion worked out, it is extremely cheap to live ( by US/Canadian standards, not as cheap as SE Asia)
One of things I like is Costa Rica has no army.
There are two international airports. LIR , in the Pacific NW has daily service to IAH, ATL, MIA and semi weekly to LAX, JFK, EWR. San Jose serves all the same with daily flights to Europe and everywhere in South and Central America.
It is a 3 hours flight to most of the major US hubs. It is extremely easy to commute out of here.
San Jose is a fairly interesting city with a great climate (3000'). There are several western run Hospitals, excellent, affordable health care is available.
I would take a hard look at Nicaragua and Panama as well. Panama has some very attractive benefits in regards to buying property ( tax exemptions and residency status)
I have been told the Uruguay is the Riviera of South America, and extremely inexpensive.
If it wasn't so far away I would live in Chile... Mtns, Ocean, Wine, good beef, and beautiful women... how does a guy beat that?