He has a lot of trouble physically, he's had a couple strokes and related circulation problems that nearly cost him one foot, then recently developed sciatic nerve/back issues requiring surgery that partly alleviated the discomfort. For him just moving place to place is the big difficulty. Hopefully yes, he will find something to get engaged in, at least mentally and emotionally. He has a tenacious attitude in general, so I think he'll do good.
I started off with almost exactly the same approach you describe. At a certain point I realized that once I reached full retirement age (67 for me) I would be fine--actually, rather wealthy by my standards if I worked and saved the whole time. So, when for different reasons I started looking at early retirement, it was the year X to age 67 or so I had to focus on. I named it the "Bridge Period" just to have a short handle for it.
So most of my planning focused on that bridge period and how I might get through it. Long story short, working to 55 would comfortably get me there. But after having spent some time here on this site and engaging in some introspection, I'm now looking at how I can move things up, which may require moving some of my full retirement assets forward in time and upsetting the "check" I had in the > 67 column.
So I reverted to just looking at 3% of the total. It's highly likely to be a sustainable level and much easier than recalculating all the various scenarios to try and determine how close I am. I'm trusting I can find a solution to the details once the time comes.
Thanks fro making me feel better about my grocery bill.
I did my first weekend shopping for May and got out of there for about $35, so it's a pretty good start. I count my household supplies and personal care items separately, so considering that and two of you versus one of me, we're probably not all that far off. Your item B) is what really drives up my bill more than anything. It plus ice cream.