SoniqCast's Aireo 2 beats its competitors to the punch: This digital music player seems to have it all, including Wi-Fi. An 802.11b radio lets users wirelessly download music to the player and acts as a hotspot locator. The Wi-Fi connection also means that users can subscribe to and receive content from Audible. It also includes an FM tuner--the no-brainer that the iPod continues to skip. An FM transmitter lets users play music from the Aireo 2 over their car stereos. And it comes with two jacks so two people can listen to MP3, WMA, and WAV files at once.
My husband has an iRiver which I think is one of the best digital music player out there. We bought a headphone splitter so we can both listen at once while on an airplane. We also bought a cassette adapter that lets us listen to music from the iRiver in our car. The Aireo includes those capabilities. We were particularly interested in the iRiver, however, because we can connect it with a wired jack to our stereo to play music or to record--we have a vinyl collection and it's nice to be able to record some of it to take with us on the move. I'm not sure if the Aireo 2 has that capability.
The Aireo 2 isn't yet for sale so price is another unknown. Also, it's for PCs only at this point.