Mac – (Batch) moving iTunes songs to ~/Music/iTunes/iTunes Music/Artist/SongName

I believe that currently the only way to do this is by setting the Album Artist. Considering that you only need to set the Album Artist for albums that you are having problems with, and that you only need to copy and paste the artist name once for each album, it doesn't seem very tedious.

The tag format iTunes uses allows the storage of year-month-day for release dates. You'll note if you buy songs from the iTunes store they frequently have the release date including the month and day. I do not know if iTunes actually obeys this data when sorting a list, but you can add it anyway, so it's worth experimenting.

The Get Info window won't let you add a month or day - there is only a year tag - but external tag editors certainly do. I had a simple one that looked like the iTunes Get Info window but with more options, I can't remember what it's called... I think MusicBrainz Picard also lets you enter month and day.

If you've edited a track with an external editor, you can force iTunes to refresh the data using an Applescript (assuming you're on Mac OS). There are other tricks that are documented here on the MusicBrainz site. The Applescript in question is near the bottom, I use it all the time after editing tags with Picard.

EDIT: Let me know if it works, eh?