Enter the Orbit Sidekick. I am borrowing my sister's Orbit G2 stroller, which I "suggested" she purchase and I just knew with as fancy as it is, it had to have some sort of toddler attachment or way to make it a double stroller. Sure enough they make a "Sidekick" which is basically a skateboard attached to the wheel of the stroller, complete with handle for the child to hold onto. Just the coolness of this alone made me buy it. And the irony that James is in fact Zach's sidekick is not lost on me as well.
Zach loves it. He thinks he is so big riding his skateboard and he gets just as much attention as James when we go places. He was uncertain at first as you can see from the video of our test run, but has embraced it now. My sister questioned if I had in fact done this myself, which she would not put past me to some how rig a skateboard to her stroller. I reassured her that no, it is an actual product and totally removable too.