I'm contemplating this decision because I'm not sure if it would be desirable for tenants to have an extra room instead just a loft area.

The sums (damages) you describe are well beyond small claims. 

We use Roku TVs in Guest mode so that guests can comfortably log in with their own accounts into whatever service they want and know that they will be logged out automatically on their checkout date.

You should be on Schedule E.

They'll be bought by local members of the communities often to house their toys, be used as workshops, some people rent them out as storage, etc.  

This deal would be $275,000 with the owner holding 80% of the loan for 5 years.  

And you don't need to be licensed if you're just managing your own stuff do you?

I will soon be operating a medium-term rental in a small city in Ohio.

I am a division one soccer player and have been blessed to be done with my last years with no debt.

Hello BP community,I am a newer investor I currently have a flip on the market trying to be sold.