My biggest concern too is, what's to stop them from going around me and just purchasing it themselves without my help?

@Jonathan Gibson- that is definitely something I am concerned about here.

I would lean towards younger if you were able to tell their finances were in order.My only concern with the older tenant is that her history shows she redlines her finances, and with the average person history shows more about someone than just their willingness to change (think about how many new years resolutions go undone).

This issue has effected me widely and created a major safety concern if I want to drive for dollars  and look for properties . 

Are there any special concerns with HOAs I need to worry about?

I have bought sfrs at these before but I am wondering if anyone has purchased a condo or knows special concerns with condo foreclosures. 

I'm not too concerned about being able to rent the units out quickly once it's renovated.

I don't foresee a problem getting out of the hard money loan, my concern is rather on the final interest rate I'll get on the 30Y mortgage (4.75?

I wanted to purchase a small commercial office building and was rejected and loan officer suggested they were concerned about what to do about current properties because of my age.

The goal is, or should be to secure income, so if the concern before you even rent is that you might have to evict a tenant, the focus should be on screening and qualifying potential tenants so as to try to minimize, as much as possible, the probability of renting to a troublesome tenant in the first place.