I had never skateboarded before getting a boosted board. It took me a week of commuting (20 minutes each way) to get somewhat comfortable at the top speed. There are three speed caps, slow medium fast, so you sort of level up after each ride or two. I don't think riding on a street is a good idea (seems super dangerous if there are any cars around), and my commute follows a separated-from-the-road bike path.

Riding is super fun :)