The catch is the deed is in her husbands name and he died a few months ago.

Hope an attorney can chime in here!

How can I place a provision in her contract that stipulates if an adult moves into the unit, not listed on the rental agreement, I will automatically increase her rent?

If I had a dollar for every time someone mentions cash-for-keys...If your investment strategy is to pay tenants every time you hit an obstacle, this is the wrong business.

I don't know if it's legal in your state for her to collect funds in her personal name but it certainly doesn't sound professional or ethical.

From a lending perspective, the risk is just inherent in the single-family home investment.

I really want to help her first and foremost but I know that I can't put any money in her pocket by selling her house the traditional way.

The only real obstacle is if there is an exclusive listing agreement in place...agents (besides being idiots in general) are territorial.

I like it this way since it makes it clear that they do not live there, so I will not be getting a call from a nosy mom who wants to be let in to snoop in her kid's apartment to see what the kid is up to. 

I agree, finding consistent reliable contractors has been the biggest obstacle.