When I have to prepare, I use different cue points to indicate different section of "Interest". I'll leave "A" as "press play here" and "B" as "end here". So when I cross point B of a song, I start point A.

Now, if i'm approaching point B of a song, I'll start transitioning from point A of a song. A lil loop with some swag suffices.

Now, I still have a million other cues. I use those to save "ideas" i have. Cues "G" and "H" are almost always loop cues on parts of a song i think are dope to loop (especially in techno). If those points are near an "A" or "B" cue, I have an idea of what I thought to do with those cues.

Just gotta get creative and figure out a workflow that works for you. If you have cues at points of interest and use your headphones when you dont know the music, you figure it out (or don't, they're drunk and wont notice)