The same people behind Pocketster, that little Pocket PC app which lets you swap and stream music files with other
Pocket PCs, have figured out how to add iPods to the mix with Pocketster Pro. It's not exactly what you'd call a
graceful solution (we'd kill for Apple to just come out with a simple WiFi attachment — or add WiFi to the next iPod),
since it requires a Pocket PC with USB host capability (Toshiba's e805 is one of the few, but there are a couple of
others, or you can add it with a CompactFlash adapter) and a couple of cables, but assuming you can get it up and
running you can more or less add WiFi to your iPod and swap and stream files with any other similarly equipped iPods
that are within range.
We'd blather on about how this is the RIAA's worst nightmare, except that they probably don't have much to worry about, at least for now. Pocketster Pro seems just complicated enough to scare off all but the hardiest of gadget geeks, to say nothing about how you also need to carry around the right kind of Pocket PC with you. What they should start worry about is that sooner or later more MP3 players will start coming with WiFi built-in (there's already one sorta disappointing model called the Aireo out there), and even if the manufacturers (inevitably) cave in and try to put some sort of anti-filesharing crap in there, some enterprising young hacker will figure out how to get around it. That's when you'll finally be able to ride the subway and see what's on other people's iPods and grab those rare Josef K bootlegs you've been looking for.