Re: Appreciate suggestions for what canoe/kayak to get.

Not quite what you are asking but raising the mast on the sailboat can
be made a lot easier using the mainsheet and pulley, if you're not
already doing so. A query on a sailing newsgroup will likely result in
photos or diagrams.

As for canoes, manufacturers offer the same model in different
materials, epxoy reinforced with kevlar and carbon being the lightest
weight and highest cost. A 14 ft "solo" canoe would do for day trips
with your dog and weigh under 50 lb. Expect to pay over $1200. For
week long camping trips with the dog count on a 16 ft canoe.

I'd agree with the suggestion to slide the canoe into the camper while
under way, removing it at night. Of course, take the camper when you
go shopping to see if the canoe fits and if you can slide it in.

Good luck and happy paddling.