How do I download songs to my MP3 player?

I purchased an MP3 player for my son and wanted to surprise him with his favorite songs downloaded from iTunes. The MP3 player is a Phillips Model # HDD082/17. It says it can be used for Windows Media Player and comes with software for this, but I am wondering if I cannot use iTunes for downloads. I don't know how to do this, though. I have purchased the songs and have them in my library, but I don't know how to get them into the MP3 player. Any suggestions? Thanks

It really depends on whether iTunes works with your MP3 player. Some players come with 'plug-ins' that add to iTunes. It's most likely that this won't be the case resulting in the following options:
a) Try using the MP3 software that comes with the player - if it works with Mac. Under this circumstance you'd only use iTunes as a means of buying the songs and ripping to Audio CD.
b) There's also lots of Mac software available for managing MP3s outside of iTunes. Have a look at versiontracker.
For example, you may find that Thrupp suits your needs:
http://www.utsire.com/thrupp/
c) Really a last resort: Drag and drop the MP3s from your iTunes library into the MP3 player. Most MP3 players will appear as a hard disk on your desktop. Provided that you comply with the way the player expects the music to be filed this should work.

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