I have a fairly extensive iTunes library that I've built up over the years and I listen to it across multiple devices - my laptop, a desktop computer or two, and of course my iPod.
I have been frustrated with the "music sharing" experience built into iTunes, so I decided to move everything to my home server as a central repository for my iTunes music that can be shared, accessed, and kept up-to-date by any computer. This will allow me to purchase a song on any of my authorized devices and have it immediately available to any of my other devices with no manual intervention. Slick.
This How-To will be based on a central Windows network share. It can be on a server, it can be a Linux Samba share, or you can simply share out the iTunes folder (the folder that contains your .itl file) on your main computer. The process should be pretty much identical, just alter the process below as necessary.
The first thing to do is create your network share. I created a folder on my home server called Share, and shared it as Media. I don't like simple file sharing, but if you use it, simply share it and make sure to check "Allow network users to change files". If you don't use simple file sharing, make sure to create a username/password combination that matches the machine you'll be using to access the share.
For example:
- My desktop and laptop both have a username of Matt and a password of supersecret.
- On the machine where the share is located, create a username of Matt and set the password as supersecret.
This isn't 100% necessary, but barring running an Active Directory domain at home, I find this the easiest way to manage my network usernames/passwords.
When you create the share, make sure to give the username you created full control under Sharing, as well as Security.


As you can see, the user Matt has Full Control under both the Sharing and Security tabs. Windows will default to the lesser of the two permissions, so make sure they are the same. Full Control is required so the user can update the .itl file and add/remove music.
On your desktop computer, rename your iTunes directory. I chose iTunes-bak. We'll remove this folder later, but you'll need it now. The folder is likely in My Documents\iTunes.
Create a drive mapping to the new share. I chose M: for Media. Just right click on My Network Places and choose Map Network Drive. From there, choose M: and in the box below that, type \\server-name\sharename. If your username/password combo is the same, everything should be mapped once you click OK. If not, you may be prompted for a username/password to access the share.
Now, let's point iTunes to the new central music share:
Single click on iTunes, hold the shift-key down and then double-click on iTunes to open it. You should see the following dialog:

Click Choose Library ... and point it to your previously mapped drive.
Once iTunes is open, it will be empty. Don't freak out! Your music is still safe. What we want to do, is open the iTunes folder we renamed earlier, open the iTunes Music subfolder, select all the folders (CTRL+A) and then drag and drop them onto the empty iTunes folder window. This will start a file copy.
Note: Make sure you've configured iTunes to copy any new music to your iTunes folder when you add them to your library.

Once the file copy finishes and iTunes finishes analyzing the files, you should see all your music populated under the iTunes Music tab.
Don't worry, the hard part is over!
Now, on any other devices you wish to connect, simply map the drive exactly as you did above, do the shift+double-click trick and point iTunes to your new library!
If you want to access this share across the internet, install
Hamachi or your favorite VPN software to connect back to your home network and voila, now you can access your iTunes folder from any WiFi hotspot as well.
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Some parts of this article should be credited to LifeHacker. They provided the final piece of this puzzle for me which was dragging and dropping the old iTunes folder into iTunes to create a new library on the share. Thanks guys!