Yes I do fear the ticking time bomb......We will have to work at finding some solution in the middle, to both keep my Mom comfortable with decisions while also doing what we can to update and maintain. 

If you close on the property and then discover the roof is leaking, the main sewer line is nothing but tree roots, really any major expense, that can easily put a borrower in a position where they do not have enough actual cash to solve the problem, so the property loses value due to deferred maintenance, or the borrower digs themselves into more debt, making it even harder to get another loan to cash me out of the equation at that upper 20% of equity.

Maybe we are both missing something.The only way I could think of that is interest only or negative amortization or something like that.I would offer an alternative solution.

There is no external damage i.e. tree falling down etc...

Had another contractor remove a small tree and debris from the yard, and one more to touch up paint on the exterior.

Some are cool spaces (like a loft, tiny home, tree house, desert home, etc.).

There was always a creative solution and flexibility for a way out when working with his team and never a ‘red light’ coming from them during hopeless times.

I needed a solution quick.

Their problem, unless the tree is obviously damaged/unhealthy.

@Gerry Magrini - Hi Gerry, as others have noted there are a lot of good tools out there that could be worth considering; but definitely look for a software solution built for DIY landlords (1 - 15 units) so you can bring some sense of automation to the rental management process (just to make things much much easier for you).