You might want to check out John Vigors 20 small boats to take you anywhere and add an Albin Vega and International Folkboat to your list. I am looking for a boat in a similar category to you and know your constraints. I have a V-8 explorer and probably have a slightly larger towing capacity than you and know of no boat in this category that will be towed comfortably by anything less than a 1/2 ton pickup with a 3/4 ton recommended. Figure aroun 5-6 thousand pounds for the boat, 7-8 thousand on the trailer.
Also concider this boat while being on a trailer is not trailerable. It will take a major effort to get this thing in the water and ready to sail figure 2+ hours. Not something you want to drop into the lake for an afternoon sail. Other thoughts may be a Montgomery 17 or a ranger 23, both light enough to tow, and capable sailors.
I actually have that book (it is a great help). What I would like to do is find a boat that is bigger and more seaworthy than my C22, but, that I can still launch from a trailer (possibly with great effort once per year). I wouldn't expect that very many boats in this range would be good for regular trailer sailing. So, the trick is to find as much boat as I can, that still has moderate draft, and probably won't get me killed if caught in a big T-storm in the middle of Lake Michigan.
Here is my expanded list:
Bristol 24 -- Draft 3'5". Standing headroom
Pacific Seacraft Dana 24 -- Draft 3"10", maybe a bit deep
Bayfield 25 -- Draft 2'11" !, too tender?
Cape Dory 25D -- Draft 3'6". 'Slouching' headroom
Pacific Seacraft 25 -- Draft 3'3". Maybe not enough headroom.
Vancouver 25 --Draft 3’10”
Cape Dory 26--Draft 3'7".
Voyager 26--Draft 3'4". Probably too hard to find.
Albin Vega 27--Draft 3’10” Maybe too deep, but, I like it.
Nor’Sea 27--Draft 3’10. Designed for trailering.
Bayfield 29 -- Draft: 3’6”! Like the head in place of V berth.
Cheoy Lee Bermuda 30 --Draft 3'8". Maybe too much wood to care for.