The house is paid off free and clear, but we have no intention of selling it; we want to keep it in the family and turn the lot into a vacation home, Airbnb, or even a rental.

What is market value for the place that was just vacated? 

You want to invest just to have a place to live and potentially offsetting your mortgage payment by renting out the vacated rooms or having x amount of cashflow in the future?

For me if it is vacation home I don’t care much about the dscr but I care lot when it is LTR. 

So when lease 1 expires in August, ask the tenant to pay $1,500 (or whatever you would be satisfied with) or vacate.

None of my friends have ever told me they want to vacation in Iowa so I don't know maybe it is.

Most units are inspected and turned in less than seven days from move-out.Within 24 hours of work completion, PM inspects to verify and updates photos to document the condition of the rental before a new tenant occupies.I aim to turn all units within seven days of the tenant vacating.

Do know even if you don't collect while you didn't get the money you wanted you stopped the tenant from taking the vacation they wanted, buying the car they wanted, renting the house they wanted, etc.

Don't vacation... use that time wisely.  

You have no liability if the router needs reset and you're in Europe for another two weeks - you don't have to interrupt your vacation to get a vendor to go into your home and fix/diagnose, or get to the secure part of a building where you store that equipment.