I've never paddled with a dog, but have heard it recommended to have a pad for the dog to lie on - keeps them from slipping on the bottom, and they will be more inclined to lie down for you

also, if I were you, I'd be training the dog to lie down on command, so that if you get into questionable conditions, it will be lieing still, not getting antsy - regardless of which boat you take

usually when I'm solo, I will take the big pack and my saw on the first trip - helps to know where the trail twists and turns and detours before you try it with the boat.  Also, if you wind up at a small landing where you'll have to load your boat in the water, its tough to find a situation where you can leave it tied off and floating in a place that will work -  I'll go boat first,  if on a well know trail, like Nym to Batch - there, I know I have a large landing I can safely leave the boat at and a known easy trail.