On the one hand, you get props for being very original.
On the other, I've done a lot of boat towing (behind my truck) and have found that boats don't pull that great as they are pretty high off the ground and the covers are horrible about catching wind and crosswinds.
I think pulling that in a heavy crosswind would be very difficult and not a lot of fun. If you were only going short distances or lower speeds, you'd probably be fine, but I wouldn't take off cross country pulling one.
2015 Honda Grom
2015 Yamaha FZ-09
2013 GL1800 ABS
2011 Ninja 250 (Track)
2007 GSXR 600 (Track)
2004 GSXR 750 (Track)