Finding the private money seemed to be the biggest challenge my friend has had while doing this. 

New built for starting out could be a bit challenging.

The challenge is, I’m not familiar with the local market—or the Mississippi market in general.Does anyone have insight into the market in this area or know of investors interested in properties in western Mississippi?

Accurately estimating expenses like maintenance, CapEx, and make-ready costs is a common challenge, especially for new or prospective investment properties.

I have read the city’s guide https://www.slcdocs.com/Planning/Guides/ADU_handbook.pdf but I still have questions.1. can tell that till require the owner to live there for the ADU. 1a is it for permanent residency or is it justified if it is a second home that I would use occasionally?

The Cape also in my opinion is oversaturated with STR's so it's challenging to find a base number of how your property will perform. 

Challenges?

Challenges?

That said, there's quite a few homes in that area that have that challenge (no driveway/street parking).

You’ll often see sales with 100-200% swings within the same area, which makes having deep local knowledge and understanding the nuances absolutely critical.I do this for a living, and even with experience, comping in Detroit can still be challenging.