What are you using as wheels, Unions?
Those aren’t round. If you are try Cylinders or Balls.
Also try changing the Torque in your HingeConstraints. Too much and wheels jitter.
Are the wheels touching the skateboard? That could be a possiblility as well.
I’ve played around with it a bit more, and it really does just seem to be the wheel size. Bigger wheels make the problem go away, but it looks funny on a skateboard. I also don’t want to solidify it and just make it slide, because players can customize it to have different textures, revealing that the wheels aren’t actually turning.