Serve your iTunes Library to your PSP via WiFi
Sure you can use your PSP as an iTunes remote, but what you might not know is that you can also serve your iTunes Library to your PSP via WiFi using Dot-Tunes on OS X. Dot-Tunes offers all your iTunes music up via a web-interface that you can navigate using the browser that's included with 2.0 and above firmware. Then you can either remotely control your iTunes, stream the music to your PSP, or download the individual songs to your PSP. Of course, downloading to the PSP only works with PSP-compatible songs, so tracks bought via the iTMS or encoded in AAC format won't work.
If you're on Windows, don't fret, as they have a version for you too. Dot-Tunes runs $29 Australian.
