I am currently working with a CPA in PR and a Financial Advisor (CFP) here in the US. Here is what I found so far:
IRA that was created in US will pay Federal taxes for any distributions as regular income even if I move to Puerto Rico. However anything you do not take out (distribution) continues to grow tax free.
Anyone with a ROTH IRA has already payed taxes, so all distributions in US and Puerto Rico are tax free. I need to clarify, but it seems all growth is also tax free. My Financial Advisor is thinking that maybe I should convert my IRA to a ROTH IRA, but we have to do the numbers, I do not care much to pay 100K in taxes for the conversion. No decision yet.
As to Social Security Benefits, here is what CPA said:
"Social security – Puerto Rico excludes social security from taxable income. Therefore you will not pay PR taxes on social security, depending on the state you live and current state tax law this may be an advantage for state tax purposes. For federal tax you have to include this as income even if living in Puerto Rico." ---- I asked him to re-explain it, waiting on return email.
There is also a twist about inheritance that I still have to clarify, it seems that the fact that I was born in PR, moved to the US and I am returning back to PR has some bearing. Not yet sure what it is or if positive or not. Waiting on more info.
*** I am working via email and being charged by the hour for answers, but I also have a face to face appointment with the CPA this coming Tuesday. So I should have more info. My CFP is free, he is a friend of mine.