Whereas surfing is all about water, skateboarding has come to be associated with air as a result of the types of tricks that lend themselves to skating. This is despite the fact that it's an earthbound vehicle, and limited, impractical one at that. Those who make skating into an art form seem to be elegantly turning the constraining force of gravity into a tool to escape from it, transiently.
I think this desire for transcendence is neatly expressed by painting wings on a wheeled plank. It reflects an awareness of the limitations, and a childish flouting of them. Naive and innocent; just daring enough to challenge what's accepted as truth.
Skaters often keep their broken boards, perhaps as evidence of their daring. They can also be seen as symbols of consequence: experimenters put themselves at risk of unknown dangers. Brave experimenters are aware of the risk of the unknown, and seek to discover and overcome it.
So what does this broken, winged skateboard say? I say it's an expression of an attempt to transcend the bonds of fear and turn the forces of nature into tools of one's will. That it's broken says that experimenters will fail; that it's put together again says they will be undaunted and try again.
In the face of the counter cultural symbolism of the skateboard itself, it speaks of experimenting with lifestyles, modes of expression, and core values. But in the end, it's just a broken wooden toy. We must be brave and experiment with new mediums of self-expression as well.