We own our primary, own a STR internationally, 3 commercial buildings, and a 4-unit apartment building - so we are highly familiar with real estate but here's a new conundrum.

Luckily enough, I had helped my previous boss at the time move from his unit next door months prior.

This would help you see its value for resale or appraisal for refinance and help determine the level of rehab needed. 

I would focus on a different intent: intent of the anti-abuse rule and its reference to "a single unit of tangible property" in (6)(i). 

I have 25 doors and I can’t tell you how many times tenants have “guaranteed” they’re going to rent my unit then back out at the last minute.

I live in one unit, rent out the other unit, and rent out the detached garage for storage. 

Furthermore, I'm curious about the level of risk associated with this process.

If depends on your level of participation with the partnership / LLC. 

I normally advise people to self manage for the first part of their journey if they can so that they can get a knowledge base to become better investors.At some point if you get to enough units self management is tough and its too costly to hire an employee so the numbers make sense hiring a property manager.To be blunt, you are going down a risky path for an investor.  

4 units in New Haven for a new investor is going to be quite a bit of work.