A while ago I had an idea to listen to iTunes Music Library from PSP, using PSP's RSS Channel. But the idea required Apache and some Apache modules which is kinda hard to deal with in Win32 systems.
So now I made a software by myself: iTunes RSS Server. It's built with Perl and you have Win32 exe binary to double-click to run as well. It has a support of both Windows/Mac OSX and it can "stream" MP3/AAC files to your PSP remotely. Smart playlists are also supported and you can listen to your "Top Rated" tunes from your bath room / bed room with Wi-Fi, for instance. Kinda neat, eh?