Though it may cash flow well based on their current debt service, when you compare the income it produces to the equity they have is it actually even a good investment for them from an ROI perspective or would they be better off liquidating and redeploying?

So based on that I guess I'd have to pick Detroit.

Based upon the screenshots of the software it looks like Investor's Edge software is just a white label of Propstream. 

For example Hospitable has a option for this through there direct bookings payout sections but it is only for specific states.

Wilmington: smaller than Greensboro, but has more of a tourist base since it's on the coast.

Yup, property condition, vintage, neighborhood, tenant base, property management are all very important considerations. 

Even in HCOL areas, adding an ADU typically does not make sense because developing a single small unit is the most expensive residential development that exists.Adding an ADU is a lot of work (probably more than a brrrr but with worse return), has poor financing options, typically adds less value than the cost of the addition, and detracts something from the primary structure even if it is just yard and privacy.Good luck 

The investors must be provided a Private Placement Memorandum, subscription agreement, and operating agreement.  

Most who opt for section 8 are purchasing in the lowest barrier neighborhoods where section 8 is the best of bad options.

At least you have the option of saying yes or no before it is sold.