Please put your input on whether or not this seems feasible, I need the good comments and the criticism so I know exactly what to expect in the worst case scenario. 

I think, unfortunately, your friend made some very critical mistakes that are going to cost him time and money.Here's what I see as the steps to unraveling these egregious errors:(1) Hire an attorney whom specializes in landlord/tenant law(2) Wait for the eviction moratorium in NYS to end (patience will be required here, as we're at 16 months and counting)(3) Under your attorney's advice, carry out an action against this freeloading occupant as a "licensee"  (I think it's called section 425?

A critical component of the CARES act of 2020 helped multifamily borrowers with agency loans by providing a forbearance period at no penalty.

It's not to criticize, its to help. 

I enjoy taking photos and have a critical eye for issues as well.

When you find what you think may be a deal, bring it to us for critical evaluation.

for best oceanfront house dals for STR (I actually research OBX and cash flow there works the best, although it's an opposite coast for me so less lucrative for the first real-estate investment)- Take into account the need for good management/cleaning services as for STR it's critical to keep the property up to standard in between rentalsAlso, I have an additional question on the CapEx for STR vs LTR, does anyone here have some experience to share?

So cash flow will be more critical than passivity of the investment.Thanks in advance!

Being around people who will help you reach your goals is critical. 

If that condo collapse did not tell everyone on the face of the planet that inspections are critical and HOAs don't always do the right thing at the right time, then just go home.Your buyer isn't under contract so you have nothing.