But, at this point, he has stretched his savings and debt limit by acquiring these two houses within two years.I guess he can repeat this process again and again, but, let's assume he wants to buy a third house 45 minutes away in another town where the return on investment is better.

My point is that private lending terms are as unique as the individual lenders and as state laws allow.You have several options, depending upon the amount of control and safety you want.

Sometimes HOAs may put in unique restrictions in order to preserve the perception of the building, such as "50% of all units must be owner-occupied".

There are a lot of good TK and non TK providers on BP, all with a Unique Value Proposition.

The house is in pretty decent shape, it needs paint, the carpet needs to be cleaned and re-stretched,  some misc cleaning, and yard work.

Absent some kind of extremely unique plan that was bespoke, no.

As your probably remember from the buying process, condo's have some unique factors when it comes to the buying and selling process and there are some key elements involved that don't apply to selling a single family residence for example. 

Hard to know this home's value because it's a bit unique for the area, but our best guess based on the most similar comps around would put it at $90,000 pretty easily, possibly more.

In my professional experience (I'm a commercial broker), the strongest local residential rental market is downtown due to the college, MUSC, and the law school all being blocks away from one another, as well as the uniqueness of the downtown area. 

I stretched going up to a $470,000 all included.