Trouble syncing music with Itunes library

Dear Sir/Madam,
I have roughly around 138GB of music stored externally onto a 1TB hard-drive. There are a few problems that i have got though with this music and i need some help:
1. When i tranferred some of the music the pathways were lost, is there anyway that i can sort out the music without going through each track one by one.
2. All of the music has been collected over various laptops over various numbers of years and therefore it is all randomly sorted on the hard-drive in different files and folders, is there any quick way of being able to collate all the music into one place without going through to each files place and changing where it is stored.
3. I dont want to create copies of the music that i have already got!
Thanks for your help,
Ashley hards

Try this previous discussion:
iphone could not be synced sync session failed to start...: Apple Support Communities

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