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Using multiple MP3 Player With iTunes

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I'm new to iTunes and have a Sansa MP3 player that I want to give my young son. I would then buy an iPod for myself. Can I transfer songs back and forth to multiple MP3 players (not necessarly iPods) from my PC without purchasing the same song again? In other words, once I buy a song, can I sync it to multiple palyers?

Answers

Content purchased from the iTunes Store is in a protected AAC format except for EMI songs, which are unprotected AAC songs. Neither format will work on an MP3 player without being converted; see here for instructions on converting an unprotected song.
A song can be synced from the iTunes library to any handheld player capable of using that format without needing to purchase it again.
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