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I personally might tend towards the looser, more reactive approach; however, depending on the mood, I definitely do love something that's very carefully planned and weaves the looseness together in a more controlled manner. The early 2000s Metheny Group stuff I particularly liked. As well as a lot of contemporary large ensemble writing... but I definitely lean more towards the Mingus, Monk, Ornette school of thinking. Another great example of being loose and comfortable within a pretty controlled environment would be the Avishai Cohen trio stuff. (https://www.youtube.com/watch?v=JVijn6v_cLM - very complex metrically, harmonically - but it still feels very organic and natural)