I would spend a lot of time acclimating the dog to the trailer. My girlfriend used to take her pug to work in a burley; which he didn't care for at all. Most memorable ride: being stopped at a road crossing, another biker said to her: "Lady, thats the ugliest kid I've ever seen!"

Same goes for camping. Is the dog kennel trained? If so, having his own tent may work well. If he's more people focused or has abandonment issues, he might be better off in your tent.