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-I went to the "iTunes Music Library" folder on my Mac and just copied over the folders (albums) I wanted onto a usb thumb drive. It's only got about 20GB, so I couldn't go crazy, but it's still a lot of files. Of course the "Greatest Hits" folder had about 10 CD's in it, but it seems the BMW got it all sorted out.
-Load via USB under center armrest. You can go to the "Media" area and should see the USB device show up. You can play songs directly from the stick and as they're playing, you have the option of saving the files from the entire USB. It takes about 20 min to get everything over. There's a small "25%" indicator next to the display that gives you an update on the upload status. The upload will even continue if you have to stop and restart the car later….it picks right up where it left off.
-I'm not sure but it seems to be handling my Full quality, AIFF, .mp3 and apple lossless files fine. I believe I've seen apple purchased songs make it over. Will try and verify more later.
-Try and do all your uploads at once…otherwise the car stores each upload as a different "device" (usb1, usb2, etc.) Which gets confusing.
-I made some mistakes on my selections and had to delete the entire music library. It's an option under "Manage Music Collection" Note, this takes awhile to delete, so give yourself time if you need to delete everything.
-There does appear to be a "Random play" function, but like many things in iDrive, it's not very intuitive and you have to hunt for it.
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