I think there may be 3 main stages of a DJs cycle:
Stage 1: Imitation. Playing songs and transitions you see other DJs using.
Stage 2: Uniqueness. This is where DJs are more likely to play bizarre stuff. They want to find those songs nobody else plays, but are still learning about what the crowd can handle.
Stage 3: Intuition. The DJ starts to be able to 'read' the crowd, knowing when to change moods, how many steps to change it in, and when they are 'off'. Their 'unique' songs are now being inserted at the right times, and a sense of actual style emerges.
Stage 4: Comfort. This stage doesn't get completely reached. You are always looking to improve your collection, finese your style, read new crowds better, improve transitions, or "pick a song, push play" even better. You do, however, learn to trust what you learned in the first three stages.
In many ways, it's a similar curve to dancing (or other skills).
...It's also similar in that every DJ who reaches Stage 2 actually thinks they are at Stage 4.

Any steps I'm not thinking of?
-FF