Referencing the original post, I have 9 seasons running a 92 Overnighter that I bought in April 2008. This is a pre CV2 hull. Very seaworthy boat used in the gulf and WCVI. I have done a lot of work and upgrades and would be happy to share info/pics If interested. Lots of room on the "dance "floor". Good size for 2-3 people to fish from, handles foot and a half chop easily. Does well crossing to Gabriola, which was one of the reasons I upgraded from a smaller boat. Never had a wave come through the motor well, but have taken one or three over the bow at Sandheads.
My ideal boat would be a Gulfstream (23 ft), however at that size trailering becomes difficult due to size and weight, permits? Etc. The 20 or 22' foot versions (Adventure, Seafarer) are at the practical limit for a trailerable boat imo. Above this size operating costs go up fast for fuel, moorage. If you trailer you may need to purchase a larger tow vehicle etc. I'm sure you (OP) have considered all of these factors.
A number of people that have fished out of my boat have remarked that it is a great boat to fish out of, mainly for seaworthiness, space, layout, built in fish boxes etc. Added length in boats over 20 feet seems to go more into the cuddy cabin, so for a day fisher you may be buying additional space that is little used. My 2 cents.