Instead of jumping to a REIT or syndication, you could consider some sort of joint venture.

Find the deal first and then look into doing a hard money loan of some sort.

I am also investing in a REI software tool that will help me do the heavy lifting in sorting and sifting areas I am interested in CT.

Namely for starters, they have professional codes and requirements that force them to pass on investments they would like to buy themselves. 3) I would draw a clearer distinction of sort between "working" and "investing". ;)  Some people just don't have the entrepreneurial spirit or tolerance for risk or etc and thats okay.

I am simply seeking advice to help sort out some conflicting priorities.

You're putting all your trust in the GP, who will charge you fees for all sorts of things.

But what i am is an old grey hair 67 year old who has a lot of experience under my belt and is not afraid to be called a Fear Monger!  

I will look for a local realtor that may have experience with owner financing of this sort and maybe even know the local STR codes.

The connections will be the main thing that would hold back an out of state investor, but since you're in state, you do have some sort of an advantage there.

They had extended a couple of times to get it sorted and then went quiet on me.