Just so there's no confusion or worry here's how the canoes work (including my personally feelings on the vague-rules parts):
The canoes require 2 people paddling to move effectively, but only one "skilled" pilot. Six people total fit, so we already left over-capacity (We have six, plus Weed, who is small - I decided that he fits, but still, it is a cramped boat).
As far as rolls go, unless something dangerous happens you wouldn't need to roll to move, it's just that during exploration scenes I like to gather some rolls from people to use for narration purposes. For example, I tend to use the rolls to come up with encounters, rather than the standard method of rolling on random-encounter charts. Or I just use the rolls to narrate difficulties. Sure, sometimes I might then "punish" bad rolls with potential outcomes like exhaustion, but I'd always give a save against that.
To make a long story short, Miss Imogen CAN paddle one of the canoes with Dellrak, even if she doesn't want to. It shouldn't be disastrous. (Though I agree with her being upset by by the condition of her hands at the end of the day). A second canoe will help if any more NPCs are encountered, too.
Any questions?