It was some doctor, and when I googled the name I did find a doctor in England by that name.

There were no relatives and whatever he got was going to pay for his medical.

Hard money lenders are often wealthy business people (either investors themselves, or professionals such as doctors and lawyers who are looking for a good return on their saved cash).

I'll make the analogy again about Doctors-- They all go to medical school, but you don't go to a podiatrist for brain surgery.

Medical students or nurses or similar would also be an option.

Property tax ~$2,000/yr.The property is located in an area close to a college/medical school and 2 hospitals so I don't foresee any future problems renting it out. 

Even in Silicon Valley MFHs prices do not appreciate as much as SFHs. 401K is meant for your golden years often used for a major medical bill not covered by your insurance.So you want to jump in at market peak it will not regroup until next housing cycle facing tax consequence now?

Take other professions,  Doctor, Lawyer, General Contractor. 

The credit issue could be due to divorce, medical bills, etc, If you think they will be good tenants, why not just collect the first month rent and security deposit?  

I don't understand why Medicare is concerned with his assets unless he has unpaid medical bills but I didn't ask...is there any way around this???