Questions regarding music and iTunes

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Hey everyone :)
So, I ordered my iMac on Friday (brand new 21.5-inch 2.7 gHz i5) :D
and I have a question regarding making the move. (so glad to be finally getting a way from Windows... :p)

I have been using iTunes, and I have a relatively large music library (~1400 songs). Unfortunately, the organisation of the files is pretty awful, with album art and such in various places, as well as the music files themselves being dotted around in a couple folders, some in the folders that iTunes creates. My questions is as follows: which of all these files do I need to copy onto an external hard-drive to migrate over to the iMac when it arrives? Or would it be better just to rip the stuff from my iPod? (If so, could anyone recommend a good app/program for this?)

(Anything else pertaining to switching that anyone else is obviously much appreciated, though I have read chad's excellent post)

That's all for now,
thanks in advance,

~Nyte
 
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If I remember right, Itunes does a search for all music on first initialization? If you aren't concerned with itunes dj or ratings then you could just search *.mp3 on windows, and put all in a folder and if tagging is correct it will add it 'the itunes' way. Once over to the mac, you can also use Doug's AppleScripts for iTunes ♫ - dougscripts.com as there are a number of scripts there that make a lot of things easier in itunes/music.

You could also take a look, ask or search the music part of these forums as this has been asked before..
 

Slydude

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Many thanks Aqua and Slydude. In particular the article looks to be just what I was looking for.
Does anyone happen to know if "metadata (information such as ratings and last played dates)" includes album artwork? (as, when going through my collection adding the artwork to songs which had none, I placed it in another folder)
 

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