I've been living in the Caribbean for about 8 years and it's been very good to me. Island fever is starting to creep up, so I've started to think about other places. Next on my list might be: South of France, Costa Rica, Belize, Panama and I may even end up in Tonga for retirement.
I could settle for Puerto Rico or New Zealand, Singapore and probably Australia (all places that we discussed when a significant other was still in the picture).
Each of those countries has specific advantages and disadvantages, I don't think there's a perfect place. Re: paperwork, think outside of the box and set up a llc somewhere that employs you. Just stay current on your personal income tax and social security payments wherever you are and the authorities will love you ;)