So...as we are complete suckers, we got him a real skateboard. And the answer to everyone's first question is NO. He cannot and is not allowed to ride it standing up without one of us holding both of his hands. He mostly uses it to roll around sitting or lying down and it goes everywhere with him. He even uses it as a tray to eat when he has a snack on the couch. And this past weekend, he took it even a little further.
A few more images of the boy and his skateboard:
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