I just ordered the new Valco Rebel I.Q, it's about $630.
I don't know if it'll take a skateboard but it has a toddler seat for it that's being released next year. It has adjustable handle, is light to sterr & a good sized basket.

This is it
Valco Baby: ...because you care!

If you click onto the coloured dots you'll see it in eack colour. Hope this helps you get started.