Changing directory structure & song file locations: iTunes query

I have an external hard-drive which I have loaded with thousands of songs over the years but have never really used it. Now, I want to organise my iTunes songs but my limited knowledge has brought me to a stop... Please help!
On the external HDD, songs are located all over the place - the directory structure is bad - and I want to simplify it under a new structure. Some songs are also on my iMac's HDD which I also want to centralise on the external HDD. What is the best way to do this?
Also, I don't have any play lists organised so I don't mind if I loose the library information and start again UNLESS the library information also includes SONG information (artist, title, etc.). Could it be a good idea, then, that I simply start again? Specifically:
1. Can I just use Finder to move files around and change the directory structure on the external HDD?
2. Can I start from scratch and copy all the music files onto a new external HDD with the new, simple directory structure I want and then re-point iTunes using the "iTunes media folder location" tab? Will I lose all the song file information?
3. What do I do with the iTunes library? Is it best to "reset" the library somehow or should I do all of this moving using iTunes and therefore avoiding dealing with the library file?
Thanks!!!

Driggs wrote:
1. Can I just use Finder to move files around and change the directory structure on the external HDD?
you could use finder, but it would be far better if you'd let iTunes handle the moving and organizing.
2. Can I start from scratch and copy all the music files onto a new external HDD with the new, simple directory structure I want and then re-point iTunes using the "iTunes media folder location" tab? Will I lose all the song file information?
if you want to start from scratch, i would leave the files where they currently are. again, let iTunes handle it (see below).
3. What do I do with the iTunes library? Is it best to "reset" the library somehow or should I do all of this moving using iTunes and therefore avoiding dealing with the library file?
i would start over. launch iTunes with the option key pressed. click on +create library+. in iTunes, go preferences > advanced and point iTunes to the desired location (i.e. your external drive). in the same tab, disable +copy files to iTunes media folder when adding to library+ temporarily.
now start adding content (file > add to library). when done, go back to preferences > advanced and re-enable +copy files to iTunes media folder when adding to library+. next, go file > library > organize library and select both options like so
hit ok. iTunes will now move files as necessary and organize them. when finished, your iTunes music folder on the external drive will look like this
none of your music files will be renamed. artwork you added manually will be retained, however, artwork that came with purchases from the iTunes store may be lost. that can easily be added later on though.
post back if you need further advice.
good luck !

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