emeyex

to answer your direct question (Is it smart to sell a little low at first and start raising prices?) I'd say, it depends on your business model. (What! You don't have a business model, or not one that you recognize? I bet you're with about 60% of the people on this site.) Your business model would address such things as whether you will have repeat customers, who pays for you to gain experience, workflow, etc. Oh, and who your clients will be.

Regarding your skateboarder question: how likely are they to pay you, and pay you adequately, for your designs? It may be a thrill to think of your future life as Emeyex, the World's Most Famous Skateboard Logo Designer, but if this is a crowd that is not used to paying for such services, then you're not going to end up anywhere you'd like to be.