@tommays agreed on the setup issues. I had a small 14' racing boat that we could setup in about 15 minutes. The cat-18 we had took a bit more doing and I am sure a larger mast will take even more time.
The goal for trailerability isn't that I intend to store the boat in my driveway and head out each weekend with a new destination in mind (although that would be cool if it worked well). My goal is that when I need to move the boat around (perhaps for a particular vacation) I can do it without alot of additional services required. I want to be able to launch on an unattended boat ramp.
I intend to find a good lake home for the boat, get a slip and probably even store the boat nearby. With my cat-18 I left it rigged and stored it at the lake. This made for a quick launch.