He can't afford living there by himself and you are one car repair or doctor bill away from rent not coming in. 

I've got a strategy that works for luxury house hacking, but for most it is hard to qualifying (doctor loans). 

Make sure to take notes how to document your hours and types of activities.In the case Birdsong, doctor's wife demonstrated that she actively and extensively managed their rental properties and was therefore a “real estate professional”.

To give you folks an update:We engaged a lawyer and sent out a notice stating that 1. as the tenant modified the $500 fee if they stay after Aug 10th, the addendum is void and their current stay is unlawful2. as in our lease any repairment or alteration to the property over $30 needs our written agreement, which they don't have, we are not obligated to reimburse any cost.3. exit walkthrough would be on Aug 11th.Our tenant with a doctor of education degree replied -1. she signed the addendum so she is not an illegal squatter. 

Being young and barely going to the doctor i have accumulated a few thousand in an HSA that i use every once in a while to buy new prescription glasses or contacts.

I pressed them for more specifics about their company, and they even sent over bank statements (clearly doctored), but had a legitimate state business registration in new York.

The time you spend trying to doctor up someone else's PDF is nearly always better spent working with a local professional.

It's rented to top-notch tenants; an MD resident, a doctoral student, and a physician's assistant--all of whom are the best tenants imaginable.It all boils down to: take the house that nobody wants (but which is in the best neighborhood in town), and turn it into the house that everyone wants.Of course, the downside of this approach is that there's a lot that can go wrong when changing the floorplan/functionality of a property...tearing down walls often isn't as simple as HGTV would have us believe.

The mid-term rental would target traveling nurses, doctors, and people on business trips.  

We are also within walking distance to the local hospital, so I had thought of nurses or doctors...?