A fairly temperate climate where I can fish and work year-round.

We bought this thing, rennoed it, worked out tails off, payed it off, got hitched, in four months he developed some sort of anger management disorder, we tried to treat if for a year, but the situation was getting dangerous, so it had to come to and end. 

I'm having a hard time figuring out what the best decision is to maximize my ROI and make the best decision with this economic climate, either raise the house or buy another BRRRR property.

It is also one of the few regions in the country that is supposedly becoming more hospitable with climate changes. 

Is this a good idea in today's climate? 

We've got beautiful hiking throughout the state, access to beaches all along the eastern coast, Boston and NYC are in easy striking distance, a great airport with no traffic (Bradley), mostly wonderful schools, relatively low priced housing in much of the state, decent climate, a mostly liberal and tolerant social climate, and still plenty of corporate employers. 

In regards to the number per rentable square foot, are your units climate controlled or not?

Not sure about the climate in your area.What kind of renter would you get with no A/C?

I’ve Identified several locations within my region that, based on the trends in  residential development seem to be under supplied and positioned to be great potential locations for new climate control self storage. 

First thing I will tell you when it comes to HVAC, especially in our climate is that never take the lowest bid from any contractor down here. $250 for all the work you described is EXTREMELY low and I personally would never hire anybody who quoted me that.