very very true. u could paint it up then git it signed by a bunch of skaters like Rob Drydek or ryan shackler or something then just hang it on ur wall, then have all ur friends come over and drool over it, thats what i would do
as cool is the idea to do a custom paint job on your skateboard I can't help but notice the image you are going to paint on it really looks like a 10 year old drew it and definitely in a literal sense. I will be surprised if you're happy with the end result but do post the finished product anyway.
You should look into airbrushing.