You take the $125k you’ll have left after paying off $40k and put it in a 12 month CD.

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

Private money should be based off of the relationships you establish, therefore anything is possible.

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

Is anyone aware of any reputable lenders doing flip and hold lending with reasonable terms?

Separate from the lack of necessary information, I'm not aware of any market in this country that can support the costs of ground up construction, particularly in the scale you are envisioning  where 2 bedroom units are renting for $1400 without significant subsidies.

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.

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.