My mother is 73 and not in the best of health and finally decided to move out of her old tri-level house to an apartment with no stairs at all. This has been no simple feat. Mom lived in her home for the last 35 years, and the house isn't in great shape (euphemistically written) although the bones are solid. I think the reality was the place just overwhelmed her over the years, and she was stuck in a bad rut. I had been encouraging her to move for a long while, but it took a nasty fall to (literally) knock some sense into her. Getting an older person to make a really big change can be very difficult.
As far as projects go, this has been huge. MrsHybrid has been awesome, her first piece of awesomeness was finding just the right apartment for Mom to move into. I have played the role of project manager. When we moved Mom to her new place she downsized from 1800 SF to 1000, and brought perhaps 1/4 of her stuff, tops, with her. Mom and I spent days and days dividing rooms into keep-trash-Goodwill piles. It's not hard to clutter up a house in 35 years, and although Mom was far from a pack rat the simple reality was she had wayyyy too much stuff for one person to manage.
Downsizing has been very therapeutic for her. She feels liberated. Instead of having a house she felt she could barely maintain, now she has a comfy apartment that isn't cluttered. And she's been doing a great job of keeping it that way so far, I think she is really embracing her simpler lifestyle and seems much more at ease.
As for that old house.... To say it needed a lot of work is an understatement. The whole family has been pitching in ripping out old carpets, pulling up tack strip and staples, making numerous runs to Goodwill and the landfill, caulking and painting, etc. We have put a lot of sweat equity into the place and are now ready to turn much of it over to pros who can get it ready for the market on the hurry-up (our trusted realtor has said we'll fetch top dollar in the summer months and lose perhaps 10% in the winter months, so time is a factor). I'd say we've saved Mom several thousand dollars on contracting costs but more importantly she is in a better place - physically and mentally - now. She has been watching the changes we have made over the past year and has gotten more and more on board with the idea that less is often in fact more.