Dog Draft / Carting With My Pooch? Ideas & Advice?

If he likes it, it sounds like fun for a big, strong dog. We used to let our Sibes carry those kinds of things in a backpack. That way they aren't slowed down on rough terrain. I don't see how it is cruel, unless I don't understand the "sport". You're not going to see how much he can carry or pull like a monster truck meet or a tractor pull, are you? Sibes live to pull sleds and love skijoring (pulling their human on skis). From what you are describing, it sounds like fun for you and your dog. Can't give you any tips, but hope you both have lots of fun and exercise.