Allegedly has some ongoing medical issues.

I am a broker, inactive at this time while out of California for medical care.

Sell using the 121 exemption if you've lived in the property 2 out of the previous 5 years.  

There are a couple of exemptions to this so study it and use some advance planning and you'll avoid it fine.  

So, if the best investment today is single family homes in Anchorage and the situation changes such that condo medical offices in Houston are now a better deal, you can sell the single family homes and buy the medical condos with no tax due if you adhere to the 1031 rules.• Forgiving: As long as you buy investment real estate in a good area, all but the worst mistakes will be corrected over time through appreciation, inflation and rent increases.

I was in the waiting room at the childrens leukemia ward and mentioned to a parent how the medical bills must be hard with the mortgage.  

If your "buddy" shows up later, depending on the intent and his attempting to lease was to cover the obligation, other doors could opened, an invalid deed, an owner occupied, a wrongful foreclosure if that deed is filed contrary to his homestead exemption rights, origination of a consumer financing arrangement.....it could mount up, if a local DA get's involved, your shambled deal can go down some serious roads.

For instance, I'm more accepting/lenient when it's a medical bill in collections because those type of expenses are typically unexpected and can be very overwhelming for many people. 

I work in the medical field, which I love, but also looking to have a create a little more financial freedom for myself… hopefully through real estate, which is something I really enjoy in and of itself.I made my first investment purchase last year after doing (a little, probably not enough) research and things have been going very well.  

Yes, this applies to the medical field.