This also means that it will likely be difficult to get any long term tenants in.Because of the fact that I'm already a full time engineer, and do medical sales on the side, I'm struggling to decide if another venture is what I need right now.

Approximately a year after making the deal with her, she called and explained that she had some health problems and had racked up some medical bills.

Medical illness and  job loss can turn a good tenancy into an eviction.

If you become a specialized professional such as engineer, lawyer, accountant, or some sort of medical professional your potentially high career earnings will enable you invest in types of hands off RE...or hands on if you like. 

Now we are trying to pay off her debt & some joint & other medical & wedding expenses together so we can invest some of her income passively & create even more cash flow & long term wealth building!

I don't care about outstanding medical bills, old foreclosures, and even older car repos.

and two another item of concern is a lien for medical payments dated 2007 from Medicaid - the amount owed on this lien is not stated instead it gives an address so I will have to write or find a number.

So for the past 8 years I have been a Medical Device Sales Rep.

I would keep the medical.

Their  medical insurance just went up 200 a month.