If I were in Deb's shoes, the first decision for me would be whether I REALLY wanted to remain in that house or find something easier to live in and maintain, especially in light of the stairs, which will almost inevitably become a problem to get up and down, and the difficulty she has in getting good services where she is and her reluctance to travel more than just a few miles for medical care, shopping, etc. It will also almost inevitably come to pass that she will no longer be able to do her yard work, snow shoveling, etc., herself. The differences in what you are able to do at, say 60, and between what you are able to do at 70 and beyond, are huge.
If I did decide to stay in that house, and had the money to do it, I'd hire a general contractor and spring for the money to get it all done at once -- I mean as that is possible, over a relatively short period of time -- and be done with it. IMHO piecemeal fixing of this or that is a bad idea, as there will always be something else or the fixing of one problem leads to another (as the fixing of the tub drain led to the ceiling problem).
If I were in her shoes I know what I would do. I'd sell that old house or the land it sits on or whatever and get out from under that albatross. I'd dump all the old yard sale stuff, too. I'd find a smaller place easier to live in and maintain, minus all the clutter, and relax and enjoy the rest of my life.
But then, that's just me.