I love Windows 7 and Windows Media Player 12. Usingg this combination, I can take the music from the iTunes library, and have a choice of three conversion routes. If you simply “forget” that the source music files are AAC, by default, WiMP12 transfers the media with working metadata (ID3v2.3 ISO 8859-1) tags added, in MP3 format. They will play beautifully.
As the Clip Zip does indeed understand AAC-LC format media from iTunes, if you open Windows Explorer and select the original AAC files, it will ask you if you would like to transfer AAC, or it will convert to MP3 automatically.
Check your media first if there are compatibility issues, it’s very simple. Download and install mediainfo and it will add a cool function: if you mouse over the file in question, the media format information will display as a popup. In addition, the information screen at the bottom (Win7) shows the metadata when a file is selected. You can even update the ID3 tags right on the same screen view if desired.
There are two issues at play here. If the files are on the device, and you cannot locate them via Songs / album / artist, the problem resides in the ID3 tags. They can be found using the Folders view on the Clip Zip by their filename listing. If the files don’t play after locating viaFolders, the media isn’t AAC-LC, or it’s protected M4P media (DRM).
iTunes can be a real pickle. Be sure to update iTunes to the latest version while you’re at it.
Probably the single simplest trick is to transfer a few albums at a time at the most. See if they play correctly. Transferring a huge batch of Itunes media en masse is, quite honestly, an invitation for lots of potential issues, as it’s a real pain to locate where the problem resides.