I started with having her just get in the trailer while it was on a stable wood platform and with treats. Then we moved to walking the bike around our property with her in the trailer. Then slowly around the sub division and then onto the streets. Keep in mind she is an Australian cattle dog. Anything new takes about 10 minutes to train. We have sense put on hundreds of miles bike camping / touring.
This is AWESOME. Can I ask you how you trained your dog to like the bob trailer? I have a blue heeler and a bob trailer myself. He was alright for a little bit, but got a bit scared after a mile or so.