Ideally, I have two houses that I would like to pay off (and I have a major renovation of a third house that will happen soon).

but sure ideally in CT or surrounding states, but again... we will go anywhere for the perfect building

The original business idea (an internet business) failed, and now Im left with $70k from liquidating the assets.

I have worked hard to build up a very loyal customer base so I can be choosy in whom I deal with. 

Best Real estate agents you know with experience in working with investors and ideally who personally invest in real estate1.

I think I may have asked them years ago but can’t remember.My ideal situation is for the property tax bills to come to my home address especially the assessment notice so that I can appeal if necessary (I pay the actual bill online and know around which time of year to pay).And then for any issues with the city/county to go directly to management. 

Then where you decide to live, go ahead and house hack ideally a 2-4 unit property.

This way you don't have to trust internet friends to start out and have more oversight.

Most contractors I know in this area are sitting on less than $10k in personal assets total (except their tools, haha), so the liklihood of them being able to actually pay instead of "going bankrupt" is questionable.So, from a few years down this road speaking back what I would encourage you to do is:  Figure out the process to "make it right" with the city, ask the contractor to pay for that (pay you back ideally, since they couldn't be trusted to do it right the first time), and then kick them to the curb. 

Anyone know of a website similar to bigger pockets on the internet, but for stock market investing?