Agreed. Just as with consoles, 'Next Gen' is now current gen, so the quaifier is no longer necessary.
He pushed it too hard and didn't realize that by the time it gained traction, the term would be out of vogue. I mean, at least when Pat Riley trademarked three-peat, that could happen again. There won't be another Web 2.0 after this iceberg melts.
If you take a look at the charts of top visited web sites, you'll see that the answer to that question is quite clear and that the Web 2.0 has conquered the Web.
Now, the fact that a trademarked search term 'web 2.0' is losing its steam is O'Reilly Media's problem since that's their property. You could say that Tim O'Reilly has been pushing it so hard that he was too successful at it.