I only pull from the side of the boat because that’s where there’s a handle/tie point - something centred behind the outboard would be ideal for towing, but then when you stop it falls down by the prop and I haven’t found the side to be an issue - I’ve played around a bit with rope length. Too short isn’t good. Soon as you get up on plane, the canoe rides over your wake and then starts surfing around getting pushed and very erratic directionally. Lengthen the rope and you can go faster, and the canoe still stays up on top of the wake, which is what you want. The wake even helps smooth waves, other boats wakes, and the canoe actually rides pretty smooth up there. I usually strap a backpack in there behind the centre yoke - helps keep the rear end down and stabilize it. Also do two canoes sometimes works quite well