As above, if the canoeists are good there really should not be a problem as far as speed goes. And canoes have done the Maine Island trail - but they are pretty good canoeists and are fully set up with float bags etc.
As far as conditions and rescues if needed, the answer is the same except that it also goes heavily to your own rescue skills. A kayaker can help rescue a canoe using very similar techniques to those used with another kayak, except for minor details like having to pass the canoe more fully over your own hull to dump out the water. And being a bit more secure in the balance in your own kayak to do so - I find that in my lower volume sea kayak I am sinking down a good bit about midway in that process. I would not recommend trying this without spending some time practicing rescues with a variety of canoes because there are a few minor diff's that you don't want to be figuring out the first time in significant wind and waves.
If your experience with these folks is that they are not particularly skilled canoeists, I'd look to that alone as an issue because it could affect handling problems on the water.
Touring Kayak Paddles
Hardshell Kayak Sail Rigs
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