ITunes + external hard drive + iPod movies = headache. Help?

Hey folks,
I'm in need of some assistance. In theory, this should work just fine. But iTunes and I have a history and it's not cooperating again.
Present setup:
-Macbook (with a hard drive that is almost full)
-Music is saved on Macbook
-All is well
What I want the setup to be:
-Brand new WD 500 GB External hard drive
-An iTunes folder has been created on the external drive
-All my music was copied from my laptop to the external drive into the iTunes folder
-iTunes was updated with the new location
-Everything is fine UNTIL I unplug the hard drive, at that point iTunes resets itself to the Macbook folder. When I plug the external drive back in I have to reset the preferences to that location again and it updates my iTunes library - which is a pain to say the least.
It gets slightly more complicated at this point ... I'm in the midst of moving roughly 60 movies onto my iPod. I have a folder on my external drive named "iPod Movies." I was able to transfer 27 movies onto my iPod just fine last night. Now, when I transferring movies into iTunes I get this error, "Attempting to copy to the disk "My Book" failed. The disk could not be read from or written to."
Basically, I want my external drive to be my iTunes/iPod drive and it certainly is not working that way. Any and all help would be greatly appreciated.
Thanks in advance!

Set your folder structure on the ext HD to mimic what is on your Mac - iTunes>iTunes Music> etc - then make sure that the iTunes Library and .xml files for the library are on the ext HD. Then when opening iTunes hold down the 'Option' key and direct iTunes to the ext HD.
MJ

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Hi Guys.
I like my iTunes library to be clean and neat. I have about 2,800 MP3's and it took me over a week to "edit" all of them and "clean them up" (properly spelled Artist, Genre, Album title, etc).
Now that everything is clean and neat, is there anyway I can copy my iTunes on to my external hard drive?
Should my computer crash, or I get a new one (this thing is OLD), I don't want to have to re-organize my entire iTunes library.
Any help/info is much appreciated.
Thanks,
Vic

StubChain - Thats interesting. Will try that. Thank you.
StarDeb - Thanks again. Sorry to sound illiterate here, but how do i "drag" the iTunes folder to the EHD?
I know how to drag things, but I'd have to minimize the C Drive window, and then open the G drive (EHD) and not sure how to DRAG when i has to relase the mouse to open and close folders.
Assume Copy and paste would work??
what about what your article said yesterday about clicking on "keep itunes organized". still need to do that?
Guys, thanks for the help, and dealing with me. I'm iTunes illiterate.
I still don't know how to get a downloaded song from "My Documents" (where they DL to) over to iTunes. lol
one struggle at a time.
*I've also tried to reward with the "helpful" tabs to you both, and an error happened. Will try again...promise...I'll just hit SOLVED.*

How do I replace my old external hard drive with a new larger external hard drive and move my music so itunes can find it?

How do I move music from an old external hard drive to a new external hard drive and have itunes find it?

If you have a time machine back up of your current drive you can do this
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From there go into disk utility, format your new drive too, osx extended journaled ( I think, double check that, its been awhile since ive had to do this), hit format
Exit disk utility and then you can use time machine to copy all your exisit data to the new hhd and then your pretty much done.
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No one on the internet seems to have this problem; everyone wants to use their ipods to restore their songs and movies. Since I own an iPod Touch, restoring the pitiful amount of files I have on it is a waste of my time, especially when all the files from my iPod are sitting right on little old hard drive #3 anyway. Citizens of the interwebs, here my plea: I require a solution to my problem of getting iTunes to recognize the folder of data it once interfaced with so seamlessly. I require a solution that does not destroy four years worth of playlists, and preferably not the "date added" data on my tracks either. All other data is fine for me to lose, but preferably not. I already know that finding the tracks manually keeps all data intact. My first inclination is that a solution to my problem may be to speed up that process. For those who seek an answer, as I do: godspeed, brave mac users. God.... godspeed.

This should work:
http://support.apple.com/kb/HT1449?viewlocale=en_US
BE AWARE THOUGH:
I followed these steps and had a strange issue come up. I don't think it was at all related following the steps above. But just double check your music BEFORE you throw out any of the music from you computers hard drive.
Here's what happen.
Some of my music forgot what file type they were. I had some that decided to be plist others jpg others something else. It was totally random. And a HUGE pain to replace the music. But I worked through it.
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Kieren,
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