Update 10/20/14: As you may have already realized, the big Wear update hasn't come out yet. Delays do happen. According to several sources we've spoken to, Google will announce something soon, and the update likely got pushed to early November, possibly to coincide with the final Lollipop release.
Yep, you're reading this right: Android Wear 2.0. It's happening - and soon. According to an unnamed source, we're going to see OTA updates for some Wear devices on or around October 15th. We don't know what's in Wear 2.0 (but GPS and Bluetooth headphone support are good bets), which devices are getting it and exactly when, but it is happening. We also can't be sure Google is going to necessarily call it "Wear 2.0" - more that this is going to be the second major release of Wear (though it's entirely possible Google will call it Wear 2.0). This update was referenced in a recent CNET interview, but no release date was nailed down aside from a minor update expected later this week.
We're keeping this one short and simple, and the information is, we feel, very credible. Unfortunately, we can't publish the direct evidence for this rumor for a number of reasons, but we're very confident in the reliability of our source here.
What's coming in Wear 2.0? Probably a lot of bug fixes, and likely some new features, but we don't have specifics at this point. This update will seemingly be timed well with the release of the Moto 360 and G Watch R, Wear's two first "fashion-forward" watches, so it could be related to readiness for this new hardware. We'll just have to wait and see.