I have a pen drive of
8GB!!!, and a girlfriend who hates most of my music.
This is an effort to have three playlists:
P1: All tracks on the pendrive.
P2: Few tracks out of these that appeal to women (sting, collective soul etc.)
P3: Few tracks that appeal to old folks (classical Indian stuff).
Simplistically,
P1 = Metal + P2 + P3
So anyway my solution for the time being is three folders:
F1 = P1
F2 = P2
F3 = P3
which means that songs in
F2 and
F3 get repeated in
F1 - not a big deal, until I start running out of space!!

Then it makes no sense to duplicate tracks (and tracks at 320kbps are around 11MB each).