Moved 9.2.1 library to new computer, can't authorize or sync to ipod

Moving from 10.4.11 to 10.6.8.  Current version of iTunes is 9.2.1 (I tried 10.6.3 and it crashed three times in a row, so I went back to what I was familiar with).  Everything went smoothly, all the music shows up, all of the playlists are generally correct (a few smart playlists forgot what some of their fields were supposed to be and reset to "Music").  The two problems I'm having are authorizing any AppleID, and syncing to the iPod.  I don't know if these are related.
When I try to authorize the old AppleID, we have about 70 or 80 songs purchased through an older AppleID, I get a -42408 error.  I checked the Shared Folder, ran the terminal sudo code from the support site, and then deleted the SC folder.  Still no success in authorizing the old AppleID.  When I try to authorize the current AppleID, all the same problems.  App Store does work.
Next problem is syncing to the iPod.  First time I tried everything seemed to work right, iTunes reported several gigs of music and a bunch of podcasts on the iPod.  When I ejected it, no music, no podcasts.  When I plugged it back in, all of that space was filled with "Other", and it warned me that I didn't have enough space to sync the playlists I had selected.  Restore.  Sync.  iPod can't be synce, files are in use.  Restore.  Can't restore, files are in use.  Disk Utility.  Erase.  iTunes.  Restore.  Can't restore, files are in use.  Quit everything and restart.  iTunes.  Sync.  Can't sync, files are in use.  Restore.  Can't restore, files are in use.  I even tried deleting the iPhoto iPod photo cache.  Still nothing.  What do I try next?

Have you played each track at least once within iTunes before you try and load the track to your iPod? If you haven't played the tracks once, try doing that and then see if they'll load; they may not be correctly authorized.
Hope this helps.

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