I'd create two directories, a lossless and lossy directory. Music on your PC/Winamp/SB is linked to lossless path, and your MP3 software linked to lossy path. That way you don't have duplicate lossless & lossy when browsing SB or Winamp. But when you open itunes you only have lossy. Use something like dbpoweramp to covnert flac to mp3 as needed to lossless directory, load up itunes rescan your lossy directory.
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