The Admiral and I are approaching 70. We're still sailing because we love it and we love the places we visit, near and far. The age thing is really an issue of strength and agility - both of which you start to lose with age. The strength thing can be largely accomodated with mechanical advantage. The loss of agility is a bigger problem.
As for anchoring, I've added a bow roller and keep the anchor there when cruising. Previously, the anchor lived in the hole under the cockpit, and was lugged fore and aft as needed (or not). I have not felt the need for a windlass to raise the anchor.
Mainsail? Check your halyard sheaves - they do wear out. I was having trouble getting my main up and down, and found a bound up sheave at the masthead. Took two big screwdrivers to pry it out of the masthead after removing the pin. A new $.49 bushing restored the main to easy up - easy down.
I'm the one who's still agile - the Admiral's feet, ankles, and knees are betraying her. We've moved the boat from a mooring to a slip with floating docks to facilitate her on/off. I let her negotiate the cost with the yard owner - I don't want to know the cost. If she's happy, I'm happy.
The Admiral wants to go back to Maine next summer. This delights me no end, but I think I'm going to look for a teenager to go with us like we did in 1999 and 2001. Yeah, they eat a lot but can be good company and can make up for some missing strength and agility.
Enjoy your sailing!