The short term rental market is heavily influenced by cash buyers from Brazil and China who are snapping up new construction "McMansions" to offshore some cash.

So could go from bad to worse, it's a gamble.

This feels like speculation/gambling not investing.  

But that is an expensive gamble that I would not take with my business.  

REI is a lot like playing poker, and not because they are both gambling. 

If I were a gambling man Mike, and I were looking at CT, not just Hartford, from 3,000 miles away (with limited direct knowledge and experience), I would bet that when CT finally turns over to a more business friendly climate (ie, oust the liberal - long held democratic views), we could be just like you in CA :-) In fact, if I recall CA was in some major trouble 10-15 years ago too, and now look: 2016 San Fran became the very first area to have average home prices over $1 mil. 

Get your own off shore person for 500 per month and hope for the best, or get a pimp!

Under what circumstances can a u.s. citizen have an offshore trust where the govt cant tax money on the funds inside the trust and at the same time cant look into the origin of such funds as long as a foreign citizen is managing such trust?

Quality and security are both major concerns, and there's plenty of negative experiences shared by my colleagues who tried this route.Anything that does not require physical contact can be outsourced, including offshore. 

I wouldn't recommend going into someplace that has no policy concerning STR, as it's a huge gamble.