I don't have any real experience with iTunes integration, but here are a few things to think about. Did you re-scan your library after "upgrading" to the DRM-free AAC files? One issue may be that the AAC files need to be transcoded in your NAS to the appropriate "native" format for the Squeezebox. It may be that the NAS isn't properly configured for this conversion, or is not up to the task in terms of processing capability. In terms of the WAV files, you might consider transcoding to a "compressed lossless" format - my understanding is that WAV doesn't support all the tagging, and that might be the issue with the album art. Also, WAV takes up about twice the space as a lossless-compressed file. Normally I would recommend FLAC, but that isn't supported in iTunes (as far as I know), so maybe the Apple lossless (ALAC?)... but that's not natively supported in the SqueezeBox hardware, so you should think about what's most important to your application.
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