But like he said, it may not be critical for you very often.

Is it critical to find a real estate agent that is a RE investor themselves?

Structure is critical. 

If it is seriously critical that one needs cash then maybe the other could make small payments with no interest.I divorced my 2nd wife in 1999 (or something like that).

I understand the concept of having your contractor go in and getting an itemized scope of work, estimate materials and labor, but by the time this is done, one of you other OOS investors already swooped in and took the deal ;)   As we all know...a good deal will go quick, so I think the skill of being able to quickly estimating these rehab numbers when analyzing a "good" deal,  especially being out of state, is absolutely critical. 

Foundations of a home are the most critical.

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.