The reason I would advise against this there is often not enough deal flow to stay in that same town.

Things like w/d might help keep renters staying longer.

If said dealer operates as an S-corp or partnership - reporting is fairly straightforward.

What we did on one of these was to do the project after we learned that they were already utilizing the bedroom as a bedroom anyways (against the rules) - we didn't increase rent right away but gave them a year at current rent, and gave them visibility into what we thought market rent was going to be after some time and the option to stay at the increase... 

Those are all a minimum of 30 day stays.

So if the previous owner had stayed away from the property and just let his PM manage it I might have had less turnover the first year.  

I’m trying to stay remote to this area because it’s my first investment and I want to be as hands on as possible.

They used the system to stay in the property...please don't do it!

For instance, my mom-in-law fell last June,  hospitalized, and stayed with us till 2 weeks ago.

I can't think of any scenario where any lender in business (and wanting to stay in business) would lend twice the market value unless they cross collateralized multiple properties of the borrower in the same loan.