The best boat for you, my sailing friend, is one that will get you out on the water most often!
Ease of use
Those were my criteria, and it just so happened I found a Mk II nearby at a reasonable cost. Could not have asked for an easier boat to singlehand.
the 24' size works best for me.
[*] Sailing conditions here are mild
[*] I can trailer it (in flat FL at least) with my existing vehicle (honda van)
[*] go from parked trailer to sitting in the water ready to raise sails in 45 minutes (by myself, about 60 minutes to break down)
[*] I can single hand up to about 18 kts comfortably. sails reasonably under mainsail alone if needed (a bit of weather helm)
[*] it's got enough space in the cabin for 2 adults if they don't mind being close. I've day-sailed it in 15kts with 4 adults and 5 kids