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

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?

Duplex have different zoning that may permit additional units.

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.  

Be prepared to come in with additional cash to close due the the appraisal.   

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.

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

Additionally, I know the Waivo product for STR covers intentional and accidental damages.

A value add can be as a result of modernization or addition.

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.