M3u and Itunes

Hi,
i got my ipod today and unfortunately i have to deal with iTunes to use it. My music library is well sorted, tagged and ordered. Because of some titles are used in several CDs, i have playlists (m3u) which contain them.
I imported all MP3s into iTunes (File->Add folder to lirary) and after some hours it was done. Now i want to import my existing M3U playlists. And that's nearly impossible!
First, I have to click on File - > Import and select the playlist. After that I need to wait about 3minutes until iTunes responds again (the playlist just contains 20 song (wich were already imported in iTunes)).
The problem is that I can't select more than one file which means that I have to click over 50 times on "File -> Import". If every playlist needs about 3minutes, i have to sit over 2 hours on my PC to wait three minutes, click import, wait three minutes.. Are you joking?
The next question is why iTunes lists all files which are in more than one playlist multiple times. Hello, the advantage of playlists is, that you don't need the same file multiple times! Oh yeah, there is an option to show duplicate files, but why were they imported twice at all? And if i sync my ipod with itunes, will the same file copied several times?
Please tell me if i missed something... or if there alternatives to iTunes.
iPod Video 30GB Windows XP Pro
  Windows XP Pro  

"The next question is why iTunes lists all files which are in more than one playlist multiple times. Hello, the advantage of playlists is, that you don't need the same file multiple times! Oh yeah, there is an option to show duplicate files, but why were they imported twice at all? And if i sync my ipod with itunes, will the same file copied several times?"
There is a big difference between the music files on your PC and the song references within iTunes.
iTunes operates as a database of information for your music files. The actual music files are stored on your PC, not within iTunes. iTunes keeps absolute references of the music file location and other information in its database file. This allows iTunes to use music files from any location on the PC: different directories/folders on the main HD, another internal drive, an external drive, or a network drive (or any combination of the above). Each song reference has a specific and hardcoded path so iTunes can find and play (or sync) it. Move the file, change the path, re-map the drive it is on, and iTunes will lose the file (again giving you the '!'). Lose, move or corrupt the ‘iTunes Music.itl’ file and your complete Library will ‘vanish’.
Each Playlist has a copy of that reference, not a copy of the file. If you want a song to be in multiple Playlists, then the reference will be in each of them you select. It should be there only once.
If you have created duplicate references (in Playlists or in the main Library), then you may be importing the information incorrectly. The duplicate references can be deleted.
If you have created duplicate song files on the PC, then you are really creating extra files that should not be there.
You have not provided enough info to diagnose either issue at this point. Post back with a better description. Start with a 'Get Info' on some of the duplicates and see where the underlying file resides. Is it the same location, or a differenct location? Try many tests.

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