Odinson, The question is quantity or quality??? Do you want to live a long long time with a less than great quality of life or do you want to enjoy the years you have left having fun and being in a place you really want to be. Off the beaten path in JA you can buy land much less expensive than most everywhere in the US. Depending on who you live with (Family or alone) you can build a really nice place for way less than NA. That is the tough choice. All this is based on getting your paperwork.
I have a friend in the states who I have traveled to JA many times and we often have this conversation. I think being without a lot of money would be easier to deal with in JA then the same situation here. Out in the country you can grow your own food and herbs, fruits, vegetables, etc.. Even the downtrodden in JA are often happy despite their plight. We're not talking downtown in a city but in the country or mountains or even Negril if you can figure out how to do it.
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