Is there a time when checkerboarding is NOT desired?
ABSOLUTELY YES! If you are editing an interview, for instance, and at an edit point there is no change in background ambiance or voice quality, then do not checkerboard. This is common with a quiet setting, and less common during exterior scenes, due to undulating traffic, airplanes, dogs, and the like. I generally recommend that if you are listening on a reasonably good playback system (full range speakers or headphones in a quiet room), then the rule of thumb is if an edit sounds perfect to you there is probably no reason to checkerboard it.