Figured I'd have it shipped to the cleaner, but interested in other people's preferences. 

Yes, I feel I am in a bit cleaner environment that Jackson but I too have heavily considered to sell everything.

I self manage a STR that's 5 hour of flight away, and it's actually doable with a reliable cleaner and handymen I trust.

They may know good cleaners looking for more work

The last tenant had a suction cup mat down and whatever cleaner they used just sat underneath and ate the finish up.

I will say that if you get some ducks in a row, things like a good cleaner, handy person etc, you could manage from farther away if you find a deal or area you are interested in.

If you use the search function, there are a number of threads on this.Pros-you can rent by the room and make more moneyCons-students are often less experienced at living on their own and may do things that result in repairs (eg wrong soap in dishwasher), higher turnover, more calls to deal with things, higher chance of parties.If you do it, you may want to get a cleaner in once a week to clean common areas (students clean their own rooms and keep the place tidy, wash their own dishes) and you will need to get someone in to take care of the yard.

4) Dealing with juggling schedules because the electrician job for someone else ran over and now your whole schedule for the drywallers, painters, cleaners, is blown?

He lived on the premises and acted as the cleaner, manager, tough guy- because bunk bed renters in that area tended to be some rather tough types.

It is great you have a superior cleaner for $25 more than the average.