Rhino,

I saw Bob's set up once--Sea Sprays are a lot smaller!

Yes, I will probably need to put the mast on the trailer.

As far as double trailering goes, I've only seen it in Calif with a fifth wheel towing a small fishing boat.

Our van has been lowered to make it easier to get in and out of compared to the usual height of the 1ton van.

Photo attached of the "rig."