Or paying off my debt, while I provide them with a nice house to live in instead of an apartment. 

Networths ARV and rehab numbers are off IMHO. 

On a 2M property you should be able to write off roughly 300-400k, so that would cut your real estate income down for years, but not your W2, because I don't think you would be able to claim RE professional status. 750 hrs and min 50% of your time.

Would this be feasible in quality neighborhoods in Hartford and New Haven or am I way off? 

Obviously there are risks if I get laid off and would loose all the tax savings and be paying out of pocket for the property, but are there other things that I should consider?

It takes 2 off the table. 

Quote from @Simon Horowitz: I'd love to connect on here with trustworthy contractors that I can bounce ideas off. 

If the deal is right you can use hard/ private money to finance the home purchase and some or all of the repairs, then do a cash out refinance to pay off your hard/private money. 

If anyone has an end lender that has successfully closed a handful occupied padsplit loans and can underwrite based off actual padsplit rents I would really appreciate an intro.

In the city or more urban neighborhoods though it's definitely more commonplace.I've added off street parking behind a property off an alley like you said at least a handful of times.