There isn't much you can do to control the owner like a puppet on a string. 

Check your state laws because I think you can charge 2x the first year but after that you have to reduce it to one month of rent.More important is solid screening, then policies and procedures to keep tenants on track so they don't get out of control.

The accidental genius was instituting sufficient controls to make sure his students are doing the work they're supposed to and not coasting their way to failure.If it gets you started and improves your life, it's a worthwhile investment, for you.

- iPads or other such devices?

Prior to rent control in my market, I had preferred tenant rent, normal tenant rent, and PITA rent.  

I wouldn't offer another dime and I would strongly consider getting rid of this tenant when their lease is up.You should consider requiring renters insurance and stop being so generous when things happen that are out of your control.

I'm curious to know if anyone has ever been presented with a deal like this before and if so, are you still concerned with the market conditions in that market even though you have more control? 

Although it may not be located in CA, it is still advisable to investigate if there are any rent control laws applicable to the county or state, as Theresa mentioned.

Hire pest control and follow them around to see what they do.

They do not like being indirectly linked to an IRA they do not control.