You don't want to distract the buyers from the house with too many items or stuff.

I work for a local house flipper in the Greensboro area (Winston Salem).

Tenant chose to stay in house during repairs citing Renters insurance declined coverage.

Personally I would want to manage the rental myself at least in the beginning to make sure you get good ratings.

However, your investment in the house, officially called tax basis, did not go up.

They are trying to rent a house they do not own. 

That would be a separate mortgage and not what amounts to a second loan on your personal residence, which if you have spouses, they might not be that into. 

I personally have no connections with anyone who is involved in this niche and I'm wondering how other people have started their journey.

The ban in Asheville proper started in 2016 though, and we don't seem to have more affordable housing as a result.

I personally believe that a better way to jump into mid term rentals is to take a course on buidling a property management company or cohosting business where you bring your skillset to the table without the intial investment into all the furniture and leases.