This is great food for thought, last year the Admiral and I purchased a 41 DS and after not sailing for more than 30 years my memory of my 22 Viking is that the Viking had most everything led back to cockpit, so the only time needed to step out on the deck was to raise and lower the main, (jib had a down haul rigged), but the Viking was a day sailor with no head and a small V-berth, not really what I was looking for.
At this point I have no buyer remorse, the 41 sails very well, is even more comfortable and with its roller furling systems (main & jib) I don't really have an issue with deploying or dousing the sails. At 63 years I can see that in a few years the managing of the main sail may need some careful consideration, but that is what electric winches are for isn't it.
I guess the size of the craft is dependent on what one plans to do, are you a day sailor or are you planning on some cruising in your golden years, I vouch for the cruising aspect, have many places I would love to visit via rag and poles.