Since I was already thinking about iTunes, this post on Engadget about slurping tracks from your iTunes library to a PSP through WiFi got me into a pensive mood. While the howto that Engadget linked to is centered around a Mac-only shareware application called Dot Tunes, it occurs to me that the Internet community would be better served by an open-source application. If a versatile scripting language like Python was used, the program could easily work on both Macs and PCs with minimal changes, just like Downhill Battle's DTV.
Speaking of Downhill Battle, it seems like such an application would fulfill the requirements of their "Local Wi-Fi filesharing" project. To widen the application's appeal, it could "plugin" to the libraries of music applications other than iTunes. Their idea of a Linux LiveCD is a good one, but I do not think it would be necessary if native versions of the applications were developed for Windows, Mac, and Linux machines.
Unfortunately, my knowledge of Python is weak and I have much packing to do, so I sending this post to the Lazyweb in the hope that some young Python programmer has either already made this, or is waiting for someone to ask for it before creating it. If this does not happen, here's hoping the (living) ghost of Guido van Rossum visits me in a dream, giving me magical Python programming puissance!