Patent applications are to the tech reporter what almanacs are to the farmer. While they are never a surefire indication of what's to come, if you can wade through the voluminousness, they sometimes point to interesting things.
A European Patent Office application describes a "hand held media player (e.g., music player) capable of transmitting information over a wireless connection."
U.S. Patent No. 20060095339 describes a "portable media device" capable of browsing "an online media store" via a low-bandwidth network, and ordering the media to be downloaded to a computer via a high-bandwidth network. The patent includes a cellular network alternative for the portable device. The technology also mentions a desire on the part of both consumers and media providers to offer instant purchasing capability for radio listeners.
U.S. Patent No. 20060123052 is for software that allows the purchase of "digital media bundles having interactive content" from iTunes. The patent confirms analysts' predictions of young downloaders driven by bundled media packages.
The almanac prediction from these clues: an iPod/cell phone/radio with wireless capability that allows users to browse iTunes and order song/ringtone/video combos to be downloaded to their computer. Hopefully, a device like this one will be out in time for winter solstice.