i think they have a winner for people that don't want a two wheeler bike or are finding themselves incapable of handling a two wheeler for whatever reason. Like the Vision, I find myself attracted to the bike from some angles and repulsed by others. If I ever go the 3 wheel route this would be a consideration, as would a Lehman Vision, as would a Boss Hoss Trike. When you're ready to drop 30g on something a few thousand one way or the other is pretty insignificant.
I do believe there is a target market that will simply eat up this new model, however, like Victory/Big Dog/Titan/Boss and several others it'll never be much more than a niche brand.
Next time you talk to this guy, ask him about MPG on this machine. I've read that the old can-am's aren't very good with the pumps, i'm guessing with the additional luggage and trailer it's probably pretty poor. Not that it's an only issue but part of the fun of bikes is performance and good fuel economy(which allows for additional chrome baubles).
I've never driven one of these but I expect some of the fun of 2 wheeling is not there either, but the additional safety is nice.