My goal is to start buying rentals, and eventually transition out of the medical field over the next ten years, (or less if possible). 

Closest medical clinic is about 20-30 minutes away...and that is a clinic, not a real hospital.   

Each of these units are close to Downtown and the Medical Districts.

If you buy it today, and next year your Dad faces huge medical expenses, this house will count against him.

Life expectancy, medical technology, communication, lifestyle.

Professional Property Management is no different than insuring your property from fire and hail, insuring your car from major accident, having medical insurance, it's a minor cost to assure you won't have to incur a major one. 

@Sam DalIn Pennsylvania, Living Will refers to the document that deals with a document that outlines what kind of medical treatment you will receive if you cannot give consent.

I’ve always been successful in a college/medical town.  

@Sergey KalinaI wouldn't take medical advice from a friend unless they were a health professional(doctor, nurse, etc).You shouldn't take advice from a friend unless they practice tax or accounting.Regarding the deductions - it really depends on if the house was in service and what activity you are doing(buy and hold or flipping).

For me, I was too comfortable in my job, making decent money, good working hours and being in the medical field that has high demand i felt good.