Please.

It's that time of year when I attempt to organize my music files so I can have a working itunes library that wont a be fuster-cluck of duplicates and relocated files.

Does anyone have any tips as to how they have successfully organized things where it isn't a huge hassle?

Also, does anyone here use Doubetwist and is it compatible with an iPod touch?

I organize my ripped music files in one directory and then Artist->album->xx-songname where xx is the track number (or more recently i put the year in front of the album, such as xxxx-album).
ex. Music/They Might Be Giants/1990-Flood/01-Theme from Flood.mp3

No idea about Doubletwist though, never heard of it. [EDIT]A quick look at wikipedia says it's android only[/EDIT]

http://musicbrainz.org/doc/MusicBrainz_Picard

Wonderful little tool that will even sort out the ID tags for you, and you can set it up to organise the directory structure.

Thanks you two. For the first time in 12 years I am actually making headway in cleaning this stuff up. And an especially big thanks to Ni for linking to that program.

I recommend using 2 options in iTunes to aid you in keeping your files organized. "Automatically keep iTunes folder organized" and "Copy music to iTunes directory when adding music" (The wording on the options may be slightly different than that. I'm stating from memory since I'm on a work computer.)

This way, whenever you rip or download music, you can download it to a temporary file location, then grab the tracks you want and drag them into iTunes. iTunes will then automatically rename and organize the files into your My Music/iTunes Library folder (or wherever your default folder is for iTunes. If you're super picky about your filenames and ID tags this might not do it for you, but it's a good simple way to keep the files themselves organized.

As to the tags, there's a lot of free programs out there for managing and updating ID3 tags. I can't remember what I used before though. Note that filling in the info in iTunes will NOT update the ID tags (though it'd be nice if it did).

Hope that helps a bit.

I also vote Picard.

I vote Stop Using iTunes.