Longmont is my homebase and primary market on the agent and investment side.

With $100k in equity in your primary residence, consider using a HELOC to keep your bank account liquid and help mitigate financial risks.Discussing time management with your wife is essential.

Based on my personal experience, owners seems to evaluate two primary cost criteria when comparing PM's, the monthly fee and the placement / leasing fee.  

My brother's rental is a little over 1,000s sqft heated living area, so the ADU would only be permitted for 500 sqft in Winston-Salem, according to information I found online .One advantage of an ADU I believe would be the ability to hook up to the primary residence's utilities. 

I currently own three rental properties and a primary. 

I'm going through a divorce a determining whether I want to buy my spouse out of our primary home or sell it and split the proceeds.

Honestly if you are never planning on moving back to the house (or the area), you are not going to cash flow especially after you add in insurance, repairs and maintenance (assuming property taxes are part of your mortgage).You have a friend willing to buy it off market-double check fair market value and sell it to them.My understanding is I would pay zero in Capital Gains because it was my primary residence and I lived there for over 2 years.

There are 2 mini splits per unit- one in the primary and one in the living area.

Those aren't the primary factors. 

To me, this is something you would just buy as a unique primary residence, the only issue would be if you needed the income to qualify.