Borrowed the freeboard of a friend's friend over the weekend, and I had to say, it was pretty fun. It wasn't too hard to pick up, mostly the same set of movements. I like my highbacks a lot more than the skyhooks of the freeboard, but they did alright. I tried it around my college campus first, and it sucked. My campus is pretty much as flat as a board, and the freeboard is about as much fun as skating on a snowboard when the ground is flat. But, later we went up to a retirement community next to the mountains, which had a lot of nice hilly roads, and had actually been paved recently so it was nice and smooth. I definitely have to say that I took it easier on the Freeboard than my snowboard. Seeing pavement whizzing underneath you is a lot more daunting than the snow, because you know pavement is going to hurt a lot more. I had a friend come along, so he just drove me back to the top of the hills, like my own private ski lift.
It was pretty fun, but without any hills where I would primarily use it, I think I'll stick to the snow. However anyone in a hilly city should check it out for sure, could be very fun.