Looking at what the DMV has on their website, there are also holiday and weekend restrictions that cover most of the big holidays that fall on a weekend (Labor Day, Memorial Day, etc) that could be a real pain to work around given I will probably want to tow the boat places and use it during some of those. But you are right in that it would open up a lot of boat designs that I can't consider as long as I insist on no oversize permit. One thing I have noticed as I have looked at different boat designs though, is that most of those boats that would need an oversize permit due to width, tend to be boats I would not want to trailer or rig/de-rig regularly. Kind of like how the VG26 study plans say she can be trailered home for wintering, but otherwise needs to live in the water.
Yeah, I have spent some hours going over his site. They are tempting due to tons of interior space and a little extra speed is tough to argue with. I have similar concerns about trailering and launching from a ramp with the foldable cats as I do with fin keel monohulls. Another issue is with a monohull, I can fit a little heater in the cabin and warm all of the living/sleeping space, but on a cat with a cuddy, there are 3 interior spaces to be kept warm. Another is needing to go up on deck to access the hull containing the head late at night while everyone else is asleep. At the age my kids are right now, that would be no good, although they would certainly be old enough by the time I finished building for that to be less of a concern. And the all around visibility from the cuddy of something like a Wizard is pretty good as designed, so I could run the boat from inside in bad weather.About what boat have you looked at the Woods multi hulls? The ones that fold could fit you bill, maybe.
I'm not ruling a catamaran out, but with the above concerns plus increased build time, I am not convinced. Maybe a Wizard is something I would consider building while sailing the used monohull I will probably buy.