iTunes: AAC Lossless to AAC or MP3 upon sync to iPod

Hey, Mac gurus! Quick question for ya. I've got 8,118 tracks or so of AAC Lossless audio in my iTunes library, which takes up just under 200GB of drive space. Unless they come out with 250GB iPods, I'm sort of out of luck. :) How can I have iTunes (or another iPod sync application) automatically reencode the tracks as AAC 256Kbps VBR (for example) upon copying to an iPod?

Since I'm not (yet) an Apple scripting person, I am currently resorting to barbaric methods for batch track conversion. So far, I've tried:

  1. Switch Sound Converter: crashes upon convert to AAC or MP4, but works when converting to MP3. doesn't maintain directory structure in destination directory, and thus doesn't like multiple tracks with the same name.
  2. iTunes: create new library (new, empty location), import all AAC lossless w/o copying to library location, reencode all tracks, reimport into yet another library (so the library now only includes reencoded versions). works, but sucks.

Ironically, when I had all of my music encoded as WMA Lossless, it was easier to do a complete library convert. In Windows, I would just dragged the top level music folder into iTunes, which would automatically batch convert to the encoding format specified in importing preferences. One step. Done.