I have a few hundred albums I'm in the process of trying to setup on my hard drive. I've started out manually trying to rename each track and folder to match the album, then find the album art, but that was to time consuming.
Then I was going to use Windows Media Center as my front end and a tagging program that pulled the info from a database for me.
I was hoping I could just do all this in iTunes automatically. However, now I'm reading that unless you ripped the CD with iTunes itself, the options of pulling track info is unavailable.
Obviously none of my tracks were done through iTunes originally, so does that mean I'm left with having to manually pull the track info for each album from a database myself with a 3rd party program, even if I decided to use iTunes later?
I would look into Media Monkey, Tagscanner and mp3tag. The last 2 will only work for mp3s. If your music is not mp3 I would not recommend trans-coding to mp3. You should not have to manually have to get title, artist, album, year information but you may not be able to import your ratings, comments that you have added to itunes. Again check Media Monkey join the forum and go to the developer forum and maybe someone has a script to take info out of itunes and put it into media monkey.
Media Monkey can run VB scripts that will do all sorts of very custom routines.
Stay away from iTunes Apple has the attitude the your music is really their music and will make it hard to do anything custom like what you are doing. I suggest having artist folders and putting the album folders in the artist folders is a handy way to organize your music. I put all my artists that start with A in an A folder to further organize my music since I have thousands of artists.