Q: Keeping MP3 files in alpha order

For classical albums/pieces I always the Sort Artist / Sort Album Artist field to the composer's name rather than the performer.  I also have a Smart Playlist that selects all albums whose genre is "Classical" - this then shows all classical music, sorted by composer,

You can set the Genre in iTunes, selecting individual tracks, multiple tracks, and/or albums before doing so.  To get the best out of iTunes I suggest that you need to stop thinking about files and file names - iTunes gives a very powerful, flexible set of capabilities to manage and organize music based on metadata (some of which is embedded within files, some of which is held in the iTunes "database" file).  I've always used the options (under Edit > Preferences > Advanced) to Keep iTunes Media folder organized and Copy files to iTunes media folder ... although I know how iTunes then manages files and folders it really doesn't matter except in cases where I need to resolve minor issues.  For example, my iTunes copy of the von Karajan/BPO recording of Beethoven's 5th symphony happens to be stored in this folder:

E:\iTunes\iTunes Media\Music\Berlin Philharmonic Orchestra _ Herbert\Beethoven_ Symphonies Nos. 5 & 8 _ 'Fide

and the 1st Movement is this file:

01 Beethoven_ Symphony #5 In C Minor.m4a

but the important thing is that it appears like this in iTunes, correctly ordered with other Beethoven works:

Key thing for me is to let the metadata determine the folder and file structures and names, not the other way around.  In this example works are grouped by the original CD content, but there's no reason why you shouldn't use the Album field to divide this into Symphony No. 5, Symphony No. 8 and the Fidelio overture if you want to keep specific works separate.

Have you tried updating the metadata in iTunes instead of modifying file names?  ITunes gives you separate, and sortable, data elements for all of the information that you're cramming into a single file name.  There's no "right" or "wrong" way of doing this, but it seems that you are starting from an assumption that iTunes can be make to work as you wish it to based on file names alone - which isn't really how iTunes works (and definitely not the best way to use its capabilities).

I think that you're assuming that you would have to change the metadata one file/track at a time.  You can go to list view in iTunes, select *all* the files where the composer is Beethoven, right-click > Get Info and enter "Beethoven" in the composer field, etc.  Likewise, select all the tracks that comprise one work and set the Album field to the work name (if that's how your organizing things, rather than by commercial release).

If your MP3 files are named to a completely consistent pattern then it may be possible to use a scripted solution that parses the file names and sets iTunes metadata values accordingly (but I'll leave it to others with more expertise in that area to go into details).

Noted, though there's no auto-magic that would ever set the composer field in iTunes based on part of the file name.  That some of the metadata is set (albeit incorrectly) suggests that it is present in the original mp3s - either prior to you downloading the files or by changing the metadata values outside iTunes.  ITunes will only use a filename as the name of a track/song if the name metadata element is missing from the MP3 when you import it.  I still think that its not a huge task to correct the metadata in 2500 items - I've probably done that in the past (for live performance recordings that have no metadata and only minimal consistency of file names) for close to that number over a weekend.

What pattern scheme are the filenames in and is it consistent? As given iTunes doesn't care about the file names, only the tags, but with a third party tool it is possible to populate the tags from segments of the file path. I have a script that does this for files in <AlbumArtist>\<Album>\[D-]## <Name>[ - <Artist>].<Ext> layout (where Artist & AlbumArtist is assumed to be the same unless the optional trailing artist is included, and disc numbers are optional). MediaMonkey has some good tools for this type of parsing. For classical music in iTunes it often makes sense to treat the composer as the artist/album artist.

tt2

Hmm, so a script that takes the first word, separated by a space, from the file name and applies it to Artist, Album Artist and Composer seems like it might help. I can cook that up if you're happy with the suggested behaviour?

tt2