There's nothing in the laws of physics that precludes it. Skateboards can be extremely light and have ball bearings with extremely little friction. It's not all that unusual for a strong breeze to make a board start rolling all by itself
According to all known laws of skateboarding, there is no way a bee should be able to do a kickflip.
Its wings are too small to get its fat little body rolling over the ground.
I reckon a Pelican would easily be able to get a skateboard rolling. I'm just now sure the best steps to proceed testing it.
I'd try a skateboard at the top of a hill and see about getting a cockatoo to somehow get the board to roll under it's own propulsion so it can sit back and enjoy a ride down a hill. That'd be the way I'd try if I wanted the bird to do it repeatedly.