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my understanding is that iTunes only 'supports' wma lossless by converting it to ALAC. Someone please correct me if I'm wrong here.

WMP can be forced to play ALAC. There's a long thread on...

yeah i determined that much. I was hoping for suggestions on the best way to automate it using the command-line encoder somehow.

Or ideally any lossless files. I could do it with jRiver Media center but that's kind of overkill since i don't use that problem otherwise (since i don't think it submits musibrainzs id's to lastfm)