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.

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.

My last note would be to try to buy 3 or less replacement properties, it makes the exchange much easier and you avoid some additional rules.

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.

For a solo team we have a plan for $147/mo that includes onboarding to connect your tools at sign up and anytime throughout your membership at no additional cost, and screen share training with our team.

I'll just add that in addition to offsetting future tax liability, I'd like to offset current taxes as well, during my highest earning years. 

I agree and additionally I'd recommend going down to the store and actually feeling them.