Just some cruising around on small hills. Basically I want to get the most value for around $100. I'd be willing to spend more if it's impossible to get a decent setup for that price.
If you buy used, you MIGHT be able to get a decent set up, otherwise, plan for a bit more. You can get a new Kracked Skulls set up for about $120. The board is price point, but the trucks and wheels that come with it are highly recommended.