Re: Suggestions for my next boat
Early 90s Catalina 34s and 36 have walk-through transoms, as does the C320, Hunter Legends from 89/90 on, and yes, most any boat 2000 and on. Many had better stern platforms that did not have an actual 'walk through, ie the platform is there but you had to climb up and over into the cockpit.. so that's another option. Some CS 36Ms came that way among others. C&C 34+, 37 also had 'open' transoms..
FWIW we kayak off our boat all the time, my wife doesn't have a lot of upper body strength yet she's perfected a technique for getting into and out of the kayak on our stern ladder.. she gets one foot wet but that's it. So it is possible with practice so may not eliminate the other boats you may like.
1984 Fast/Nicholson 345 "FastForward"
".. there is much you could do at sea with common sense.. and very little you could do without it.."
Capt G E Ericson (from "The Cruel Sea" by Nicholas Monsarrat)