This all depends on what type of files you're using....which I don't think you've specidifed. id3 is an older and very restrictive type of file tag, that I rarely see used anymore, and if it I is, I write the software off as useless and move on. It has been replaced with the id3v2 tagging type that is simply horrendous but at least functional and allow you to store loads of custom data in your files.
Both of these tagging types are bandaids patched onto files that never intended to be used tagged like this. You'd be better off using Vorbis comments from FLAC and OGG files and APE tags for APE files. MP3 will only allow id3 v1 and 2, but if you're looking for help with mp3 files, I think you've stumbled into the wrong messageboard.
Anyway, I'll give you the lowdown on how you setup and use the best type of tags if you'll kindly let me know:
What type of files you're working with
What software you have (other that iTunes
and Winamp
)
What Operating System you use
Why you want to tag them in the first place.
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