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My bad, was just thinking this could make his entire experience a lot easier if it turns out he could actually fit the bike in the trailer.
I don't have a trailer, if I did I'd let you use it, but I do have ramps in Georgetown, MA you could borrow. That's damn close to Salem, NH. I'm sure we could figure out if it'd fit if you measured your bed and posted up what kind of bike. Just another option, may save you driving all over to grab a trailer. Your bike, your truck, your call.