I do need a bigger boat...but looks like I'll be carrying something around 55 pounds if I got one.  I can do it...but not sure I want to do it.  I expect I'll have to stay in camp on really windy days, no matter what; since I can't be sure the dog will stay put until he is more used to the boat and perhaps settled down a bit more.  He's going to be the type to want to dive out of the boat after ducks, etc.  It remains to be seen if I can successfully train him not to jump out on a whim.

I am worried that any type canoe will be quite a bit more unstable than the Poke boat.  In the past I have taken one of our other 60 pound dogs out paddling in the Poke boat and she does very well...stays down and keeps her weight in the middle of the kayak.

A few years ago I had to do a trip where I paddled one poke boat and pulled a cooler and other gear in a second poke boat.  That was not too difficult to do although I did not have to do it against any strong headwinds.  I was in a fairly strong side-wind which drifted the "trailer" downwind from me; I didn't have any fancy towing rope plan to oppose that.  I see one of the pods I researched had a somewhat rigid towing plan made of PVC pipe to hold the boats apart and in line.
:-?