If you have a H16 put a set of Trapseats on it and you can sail it for a lifetime and with Trapseats solo sailing is so easy. You can also put a easy mainsail on it and roller furling jib. Most people just put a furling jib on it and call it good. We have a whole fleet of H16's in our area and have some very old sailors having a great time. If you want to get into racing there is a very strong class. As for solo righting just get a Gary solo-right and your effort to right the boat will be a piece of cake. Oh if you want a spinnaker then get the trumpet spinnaker system for the H16 and you will be flying around the course.
Your best bet for older sailors (what is old?) is a Hobie Wave, why? Hard to capsize and pitchpole, easy to right, indestructible, no boards, backrests available, small size makes it easy to move around, VERY quick set up time, and best of all great fun to sail. If you order one don't order the hobie sails, get the sails from Calvert and get the hooter system that Rick White designed, and you will be kicking everyone's butt, as Rick White has done in several events with this sail set-up! Pretty fun to kick the high tech sailors butt on a roto-molded Hobie.
Just a side note the Hobie Getaway is a good choice as well but it quite heavy and so can be an issue for older person when trying to move it around on or up the beach, etc.
Good luck and most of all get a boat that will be fun!
