Besides survey issues you have to deal with HOA's, obtain tax clearance letters from the government and all deeds, except condos, must be attested by the public surveyor before closing (that in itself takes a week).I don't want to discourage you because I think investing in the islands can be lucrative, I have just seen many people from the states go in thinking that because it is the U.S. that it works like it does in the states.

If you have switched jobs and your retirement is in an IRA vs. 401k, maybe consider rolling it into a self-directed account to invest in other people's deals with that money (aka private money lender, syndications, etc.)

I’m interested to hear what people recommend in this situation.  

I always thought it was a cool idea, but anytime I see tech people get into real estate and construction (especially to this scale), I really pause and take caution. 

Also, do not compare costs over a 30 yr period - very few people keep the same mortgage for 30 years. 5-10 years is more realistic.- Overlays - some lenders may have more restrictive overlays than Conventional guidelines call for.

Thanks for the response I should have made myself more clear plan on posting it for sale in FB groups for STR owners and sellers as there seems to be a large of people looking for off and on market properties there hopefully can get lucky and find someone serious.

I know many people here feel umbrella insurance is the way to go.

My question to experienced people is should I focus on paying off this debt first then investing or would you recommend I take longer to pay off loans but also save for my first 20% down.

That is a bad thing and hurt the wallet and some people have lost homes due to this poor service.

Ask for help and ask great questions, I've found many people are willing to help.