Dave,
I am sure you have taken this into consideration already... But how long is the Kayak? Would mounting it on the trailer interfere with your turning radius, etc.?
Also, since you said the tent cannot be shifted over anymore, I would focus on the rack. REI or any kayak place sells contoured foam blocks that you can rest the kayak on to help prevent damage.
I have experimented with this same dilema, only with regards to surfboards. I have some really long, 78", Yakima bars. This way the tent sits off to the passenger side and the surfboards are mounted next to the tent. Same as H. Except surfboards cannot be mounted/transported on their sides. And it was really freaky driving down Mex. 1 with my surfboards hanging over the driver's side by a good 10" or so... Especially with trucks coming at you full speed.
Good luck.
By the way: sit on top? tandem? single?
Congrats anyway.