There are many retired folks at our club, some long time, some newly retired. The consensus of most is that sail handling for those that are not as agile and strong as they used to be should be in mast roller furled mainsails and roller/reefing headsails so many (about 1/2) have purchased newer boats with those options. The retiree's boats range in size from a Catalina 270 to a pair of Beneteau 40's at the top end with everything in between. All of the larger boats have an anchor windlass, all have all lines led back to the cockpit, all have dodgers with the exception of the C270, all have bimini tops, a few have AC. None have electric winches, one uses the Milwaukee drill technique although I was a witness of the drill smoking trying to raise a main sail on a Hunter 35.5.
There are also a couple that are old school, boats in the 31-36 range that have traditional main sails but RF head sails.....I can tell you that those folks are also the ones that appear to go out much less and whose boats are in somewhat shabby condition. Hard to say if money is a factor or something else? Maybe they are just winding down.
All of that said, I am amazed at what some of the "older" folks do as far as sailing, conditions, etc. They certainly give my hope that I'll be doing this for a bunch more years. I can't find any trends, any common additions to help with boat handling etc. It appears to me that this entire process is one of evolution with a strong dose of "whatever works for you".