Its a philosophical question, obi-wan. Are you flying the kite, is the kite flying you, or are you flying with the kite?!?!?
I love Matt McGee's article on this idea.
With our frequently rough and in-land winds, I often have to go with what I think the kite will do at that moment. If its in position for a double-wrap (low wind, nice horizontal setup), then I go for it. If the wind just went from 8-14mph then I forget the rollup, and go for a cascade or comete.
I can try to force the kite to do something its not ready to do at the moment, but it may not work and often doesn't look good if it does.
My favorite flying is just total freestyle - listening to some loud music and just losing myself in the moment.