Keep an eye out for an airbnb possibility - mother-in-law suite, etc. if you live in a conducive area. 

I purchased a house less than a year ago fro 280K. Since then it appreciated by about 20K. Also, I put in about 20K of improvements in it.What's the best way to make the transaction and minimize the tax burden? Should...

As a former VA employee and a mother of a son who is a Navy veteran taking advantage of the post 911 GI bill for schooling, I have to say at least some of what your tenant is claiming in terms of not being able to pay the rent sounds like what comes out of the south end of a horse going north.Depending on what your rent is, the BAH from his GI bill should, alone, cover the rent. 

The widow is in poor health, and the son is focused on taking care of his mother. no current income/expense data.

Not sure what your mothers situation is but she should be able to contribute something toward her own rent.

I am a joint owner with my mother on the property she lives in.

Owner was living with their ill mother.. they have done work over the years (new roof, new AC, new floors, painted, etc), but I have reservations about the fact that they have owned it so long with no-one living in it.  

I found a good property with a mother-in-law in the basement with a separate entrance. 

One I bought from a neighbor , one from a drive by while doing service calls , one from a customer , and one from a friends mother after she went to assisted living . 

The family ( mother/father in there mid 30's and 3 year old son) said they felt fine and no one vomited so they didn't go to the ER.