There are a plethora of CT based real estate Invetsor meet ups you should get involved with.

STRs are a great way to make money, that's for sure...but it does not come without risk.

Here is the BEST way to develop an understanding of the risks and rewards of redeveloping your propertyBEST - Hire a CRE - Counselor of Real Estate to do a complete market analysis.  

I imagine that the list is short and full of risk.

And as I explained earlier, your investment is protected by real property, so your risk is extremely low. 

There are those on YouTube who are very close to violating the law, if not dancing all over the line.In my opinion, the real problems originate when the buyer isn't clearly disclosing the risks to the seller, or violates the Consumer Protection ACT, or doesn't have enough capital to make the payments, or does equity stripping, (some equity stripping is legal, some is not)  12 U.S. 

My point is this, I am actively involved/advising this investor, providing local vendors contacts (handyperson, surveyor, painters, etc) and I "don't wait for them to call me", I call them weekly. 

Taking the risk of a tenant while you yourself are renting is not optimal in my opinion.

At the risk of sounding too dramatic (but I know us on BP can get extreme to reach our goals), I am going to NOT get another residence.

The founder appears to have been involved in businesses outside of real estate: ‘My dream is a locally made grooming products business’ | People | nashvillepost.comSo it does not appear there is a lot of track record there, but those are questions I would ask.