I'm faced with this idea in my own family, but I'm seeing it early. My brother is doing what I term chasing unicorns: instead of working and planning, he's living off the generosity of my mother. The problem for him is I'm now in the position of being mom's fiduciary. I'm slowly restructuring her finances so she knows how much money she actually has. For my brother, this means reducing his income. I'm going to keep doing this until he has no more income to support himself.
At least that 90 year old woman did what she had to do. Soon, my brother will be doing the same thing. My brother and my parents made a series of bad decisions to get in this situation. Now I'm left with the task of fixing it. How that 90 year old got into that situation is unclear, but I agree, it was poor planning or no planning. Bad luck is not a thing.
It is unfortunate that you are left dealing with this.
He might see it differently right now but you're doing him a solid.
Bad luck is not a thing, but setbacks are. A couple or few can really make one paddle to stay afloat, and moving. Hard to say why at 92 that woman was working, but I've run across it occasionally.