You are right retirement does mean different things to different people, some think their current line of work is retirement.
I am a typical baby boomer @ 54 with just a year remaining before I am eligible for retirement. I plan to sail until my health gives out, maybe 70 or so depending on my legs and how seaworthy they are. Five years ago I was more fit than those half my age but a couple blood clots have me re-evaluating myself. I am still very robust for 54 and still have most of my body building effects intact just need to get back into it to regain the strength. I am almost finnished getting my boat set up for single handed sailing and feel that is the most important aspect for retired sailing. I find it too inconvenient trying to round up any crew and my wife will work a few more years than me then join me, but even then I cannot expect her to go every time I do. So consider that you may require a solo sailing set up. (lines aft, auto pilot, roller furler, lay jacks etc.) As we age getting in and out of the boat becomes an issue, it already is for my wife with her short legs, so be sure you have a solid ladder or easy boarding system. Once on board things are easier, at least in my experience, as long as I don't have to go forward to hoist the sails, the anchor is the exception. Boats are also high maintenance both physically and financially make sure you stay fit in both areas. Weather also has a huge impact, I am in the Pacific Northwest and sailing season is realistically 6 months max, a few die hards will disagree but I have had enough of the elements to last a lifetime so fair weather sailing it is. If you are in a warmer southern clime it is a non issue.
As far as the industry is concerned they should strive to keep it affordable or risk losing business, once we retire our incomes are not the same and the toy boat will be the first to go when things get tight. that's all I can add for now but others will have more to say.