I think this generation of iPods has, if not jumped the shark, at least reached a more challenging phase in its development.
In case you haven't heard, the lineup is now thus: the iPod shuffle remains mostly as it is, except with new colors. The iPod nano has been made wider and now plays video. The "iPod classic" is also very similar to the full-size iPod of previous generations, but with greater capacity. Both the nano and classic have received some rather flashy new software. They can also both now play the same games; basically, the nano is now a classic with flash instead of a hard drive and a smaller, higher-resolution screen.
Meanwhile, the new iPod touch is basically an iPhone without the phone. (Or the e-mail, or the widgets, or most of the apps really.) It has all the traditional iPod functions (except Notes), plus WiFi, which can be used with Safari, YouTube and a new iTunes Store app. It has flash memory, in quantities a step above the nano (and iPhone) but much lower than the classic's hard drive; it's also slightly more expensive than the classic.
What strikes me about this lineup is that it's the first time we've seen compromises in the iPod line. The nano has become wider, so Jobs's original introduction—pulling it out of the change pocket of his jeans—is no longer possible; that change, however, gives it a screen large enough to reasonably watch video.
But the most vivid compromises surround the new touch. Why wasn't it merged with either the nano or classic? The reason is obvious for the nano: the form factor's too small for a usable touch interface. And the battery life figures explain why it hasn't been merged with the classic: touch's battery doesn't last as long as either nano's or classic's. My guess is that the more sophisticated hardware and software draws much more power, so they couldn't get reasonable battery life powering both an iPhone-like core and a hard drive.
The effect is to confuse the whole product line. The decision about which iPod to buy used to be simple: if you cared more about size and price than features and storage, get the iPod shuffle. If you cared more about features and storage than size and price, get the iPod. If you wanted something in the middle, get the iPod nano.
What's the simple rule now—when the classic and nano have reached feature parity, and the touch is now the most expensive, but with less storage, better features and a totally different user interface? The whole thing smacks of compromise, of a decision to just get that multi-touch iPod out the door now, even if there isn't a place for it in its current incarnation. Frankly, I think Apple would've done better to modify the iPhone so that its non-cell phone functions worked without activation and sell those at its new price to people clamoring for a touchscreen iPod.
No doubt people will be in the labs at Cupertino tomorrow trying to solve these problems, and I'll be surprised if the classic's replacement next year still has a click wheel. Still, this marks a first in the iPod's history. Apple has run out of low-hanging fruit to pick. It's time to break out the ladders.