[Osiris]

I’m not a huge fan of Apple iTunes, think it’s just to slow to be a good music player and I have no intention of using the Apple store. That leaves me with a tool that can transfer songs to my iPod Nano. Having said that I can immediately tell you that Mojo is not an application that I will be using but it could be really what you are looking for.
Mojo lets you share songs easily with friends in iTunes across a network and the Internet. Users in the same network are automatically added to your friends list while Internet users have to be added manually. Users need to create an account when they first run Mojo which functions as a identifier both in the network and on the Internet.
Users are added by typing in their username that they have chosen during registration. Added users have to confirm the new connection and once they do you get notified if they are online just like you would when using Instant Messengers for instance.

You can easily browse the music collection of users that are online in a window that pretty much looks like an iTunes window. Songs that are already in your own collection are greyed out while protected songs are red. Both cannot be transfered. Every song can be listened to and downloaded with just a click of the mouse button.
Using Mojo would in my opinion make much sense in large networks, Universities and Schools for instance with hundreds of users. It’s definitely a nice idea.
A client is available for Mac and Windows. Via Lifehacker and Make Use Of.

Share Songs with Mojo and iTunes