You have maybe one in Waterbury and one Bridgeport off Barnum. 

In the next 5-10 years could AI cause a major disruption in the economy due to mass workers being laid off?

At least with the S&P the dead companies fall off but overall RE keeps the underperforming in the mix.If one is high income then just throwing cash at the stock market over the long haul a nice way to go.

Anything less is truly not cash-flow.You want to not buy based off just intrinsic or cash-flow centric but the qualities of the property and the area.

I pay off principle of the mortgage around 13-14K a year and expect it to be an amazing long-term, cash flowing rental.

A low-cost way to do it would be to paint the walls, the garage door, and close off any access to utilities.

Mostly I want to know other downsides to commission based off sqft rather than %.

Ideally, one unit I can rent out long term and one unit for short term (3-6 months seasonally) that I might use every once in a while / on the off season.

I tell our customers all of the time, when you're steadily pursuing highly distressed leads with this criteria it's not a question of if, but how often you will contact the heir to a property who either didn't realized they owned, or they though the property had already been auctioned off by the bank or county.  

My primary residence is paid off which is why I want to get a HELOC.