Why not think outside the box a little...
YOu mention your friend skateboarding - got me thinking, why not set up a site doing custom skateboard graphic designs (pimpmydeck.com
), or how a bout's doing a few illustrations and submit them to threadless.com and see how they sell. How about contacting some musicians on myspace or soundcloud and offering to illustrate graphics for music releases - i know for definate there are LOADS of electronic music label that would pay someone to do every release for them for a consistent look across labels - might not be much, but would amount to something every time.
Why not do a set of really nice drawings and get them on flicker and subm,it to digg? Read the reaction in the comments this guy got when he did just that
Ghost in the Machine - a set on Flickr
Kerrrrching !
Loads you could be doing!!