Additionally, I'm working with the RE Ally Property management team, who was able to find a tenant to rent at slightly above market rates without any vacancy.

Additionally, based on your numbers, it should definitely cash flow. 

Additionally, the price point is still cheap enough to find the 1% rule and positive cash flow and there's amazing appreciation potential.

Duplex have different zoning that may permit additional units.

Once you have cash in hand, you can unlock the unit for 24 hours and let him move his stuff out.I would also consider charging an additional deposit of $500 or something, just to prevent him from leaving all the trash or stealing your refrigerator.

Sounds like you put in a ton of work to maximize the value, and that basement addition was a smart move.I noticed you mentioned the NYC luxury tax and some of the rental pricing challenges—have you considered expanding your portfolio in markets where you don’t have to deal with those kinds of headaches?

In addition, due to the 2 of 5 year rule there often is no need.  2) you cannot 1031 a property that has not been put into service to be an investment property 3) you cannot 1031 a flip.  

Additionally, I have $100,000 in cash in the bank, and my monthly expenses for my home and family are around $3,500.My wife earns between $100,000 and $120,000 from her W2 job, while I've recently lost my job but found a new one that pays $65,000 a year.

There are a lot of market-specific issues you'll have to grapple with and also, there are plenty of landmines in MFR on its own in CT that you'll have to be ready for, in addition to the nuances and complexities of developing something like this.

In addition, you want a separate bank account for the rental property to separate it from your personal accounts.