[QuickSilver]

I was able to train my yorkie out of this exact problem, so there is hope.

Is there a place where skate boarers hang out near your home or office? That will help a lot. Even getting used to the sound in the distance will help. I think you have the right idea, but you need to start further away. It will take him time to be able to tolerate one rolling by him on the streeet. You can take him NEAR that area, but not so close he freaks out. For the time being, I would keep an eye out for skate boarders and cross the street when necessary. You can distract and reward from the other side of the street.

Then maybe you can have a friend slowly roll by on the skate board, and then finally he should be able to handle people flying by.

I guess I'm lucky that my dog has never actually scared a skate boarder. They just laugh at him and go on their merry way. My poor guy tries SO hard to be scary.