So far I've managed to get the fist two skills done for the "Hipsterology" (Dave Strider's) skilltree: Flash Step and Unbelievably Ill Jams.
Flash Step is a simple teleportaion spell with no mana cost and a 15-turn cooldown. While this sounds like a potential game-breaker, using the spell significantly reduces your maximum spellpoints for a significant period of time. I'm still trying to figure out what the right cooldown and debuff times should be, but the concept appears to be sound.
Unbelievably Ill Jams (don't mind the typo) is a simple buff spell that increases your Melee power, dodge rate, Voltaic resistance, and overall nimbleness. The catch is that it reduces your trap sight radius to a an almost comical degree. Again, I'm still tweaking the numbers...
Now, as for the next skill... I'm a little stumped as to what it should be. It's going to be something along the lines of "You run a blog where you tell people they can be individuals by listening to all of your favorite music" or something like that, but I'm not exactly sure how that would translate into a game-play mechanic. After that skill I plan to have something involving either Lil' Cal or Sweet Bro and Hella Jeff, followed by a skill that reflects Dave's status as the Knight of Time.
Ah well, I've still got time to figure that out.