I would respectfully suggest that none of these (Compac 23, Bayfield 23, Nimble 24 or Aquarius 23) would make especially good boats to learn to sail on. Each has their short comings for your purposes, with the Compac 23 probably being the best of the four but not especially ideal. The best boats to learn to sail on are boats which are reasonably responsive, tiller steered, offer positive helm feel, and which are also moderately forgiving. Normally, I would recommend small fin keel spade rudder sloops; boats like the Ranger 23, Sonar 23, Capri 25, Northstar 727 (23) and so on.
Of course these are somewhat deeper draft boats than you have on your list. If draft is a concern, and trailering isn't, I like some of the keel-centerboard boats from the 1960's such as the Sailmaster 23, Shaw 24, or Pacific Dolphin 24 and the like.
I strongly recommend against buying a ramp-launchable, trailerable boat of the size you are considering and expecting to trailer it. Generally there are big compromises made in order to make a boat easy to tow and easy to ramp launch. These compromises reduce a boat's suitability as a boat to learn on. Its not that you can't learn on a trailerable, its just that they are less than ideal. Plus, when I have owned trailerables, I missed a lot of great sailing opportunities because there was not the time to rig, launch, sail and recover, unrig and stow the boat. Properly set up the best small boats can be gotten underway in something like 5 minutes from when you step aboard and put to bed in perhaps 10 or 15 minutes. The trailerables that I have owned or used typically required a half hour or more to rig and launch and twice that to un-rig and stow. You lose a lot of 2-3 hour sails that way.
It is never too late to learn to sail. I hope that you and your grandson enjoy the experience.
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Curmudgeon at Large- and rhinestone in the rough, sailing my Farr 11.6 on the Chesapeake Bay
Last edited by Jeff_H; 11-23-2011 at 11:06 AM.