Remember, prerecorded tracks have been through limiters and been mastered so haven't got the transients that are present in live music (yes, compressors on your aux can tame things a little but it's not comparative to a recording) - As a consequence, I would say take tracks that have obscene amounts of bass because thats whats going to give up first.
My go to IEM bass unfriendly tracks -
Free - Rudimental,
Can't Stop Playing (Makes Me High) - Dr. Kucho! and Gregor Salto (0:45 onwards - it's this track (I think Ive posted it in the thead before...)
And for detail and sound stage,
Hell Freezes Over version of Hotel California - The Eagles
As a rule, I would always take headroom - so extra drivers in the low are going to be your friend, especially if your primary concern is live use. You may prefer a lower driver count in isolation... but in a band situation, that extra headroom is going be appreciated.