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Just been through this myself as I inherited a hand me down ipad yesterday and been trying to select which songs to transfer as its only 16gb device. I do wish apple would make expandable memory slots or make them bigger to start with. Took some time and it was difficult to select which tracks to lose
Also make sure you convert higher track files to 128 Kbps
You should get over 4000 songs on 16 gig ipad