Both of these may impact your DTI.One of the difficulties in holding properties for a long time is that equity builds up (either naturally or by forcing with renovation), and I need to sell or refinance to get the equity. 

I'm more interested in the legal transfer of the money and tax implications thanI am the nature of the agreement.

If there's only a few comps you're using, there's naturally going to be a lot of error in your valuation model, so you're at greater risk of buying a home that really isn't going to net you much of anything. 

lolDo you find that the static nature of that market makes it pretty stable during downturns?

That will locate and document the nature of the problem, as well as letting you know how deep it is.

This is becoming a problem and my PM is really starting to pull her hair out.

Definitely looking for more turn key because the nature of the money is due to medical reasons.

As mentioned in an earlier response, certain types of agreements "run with the land" and certain types of agreements are personal in nature.

This is way outside my wheelhouse, most of what I look at are condos, just due to the nature of the market here.

The Red River Gorge (Natural Bridge State Park) area is fantastic.