Skateboarding is one of those paradoxical things where at a certain level of technical proficiency you can cross some threshold and become "boring". This is due to the seeming absence the things that make it interesting, most notably difficulty and dangerous-ness. When there is no struggle, no tension, no effort it can become too mechanical, cold, or dry. This is where style becomes most essential and is often most absent. Boringness can also be counteracted by spot selection. If it is gnarly or novel it won't be boring. Interesting garments can also help.