There is a Citizen by Development program that helps you save taxes for new developments but the best bet is to buy an existing property and slightly renovate.If you have never dealt with Caribbean based labourers and you have no patience... then the Caribbean is not for you. 

I bet it appreciates 2 or 3k/month over time.

But if the license is required and its a flaw on the lenders side you can bet the borrowers attorney will raise that.. 

It's a way of hedging my bet using as little cash as possible.

Physical REI is not a paper investment; almost anyone whose invested on paper numbers I am willing to bet is showing a lot less than the reality of if it unless they took realized gains by selling(into the appreciation rate) or cashed out refi. 

But that is the key with investing, you need to have your educated guess of future events, place your bet, and hope you are right.

In today's market, your best bet would be a house hack.

That is your best bet to ensure it is watered regularly. 

I'd bet that for the last 50 years, investors looking at Boulder have felt it was unaffordable, and that the numbers don't work for investors.

If you are looking for cash flow typically multiple unit properties are going to be your best bet but might require a little more work up front and there are not a lot of them around the area to scoop up right now.