I use headphones to beatmatch, not to listen to a bunch of different tracks trying to pick one out. Never used headphones when playing with Ableton since there's no need to even worry about something being out of time. By "adventurous" I was talking more along the lines of things like genre shifting, playing three tracks right over each other with EQ swaps, wierd acapellas, etc. For straight A-B house/trance/etc mixing with software I can go for hours without needing to preview anything.
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