Depressing? Yes and no. I, too, am trying to pay attention to where I will want to be in another 20 years. I've started taking better care of my health (though I need to get some exercise). I'm thinking about moving back west at some point--maybe Albuquerque--I like the vibe and the weather and it's much closer to the family I do have (mostly in Colorado). I'm thinking I'll probably want to rent a smallish place in an interesting neighborhood. I've also started talking to my kids about what I'm doing for my folks and telling them to take notes because they may wind up having to do the same for me and I'll try to be more reasonable/flexible than they've been.
I definitely want to have things set up in a way that will allow me to be as safe and independent as possible, planning for what will enable me to do that before I need it.
I do go out of my way to express appreciation to my dad for doing such great management of his money all these years. He was an NCO in the Air Force for 20 years, and a mid-level federal civil service employee for another 20-some years and he's managed to put together enough money to support himself and his wife for a nice retirement.
We all get old and die. Just want to keep enjoying life as long and as well as we can.