@Otto - That is a good step, all plugins that are left with no update for so long should be hidden from users.

But, in the same time we need some method to reach out to users and let them know about benefits of new WordPress versions. And I think that ball is dropped with that since WP 3.0, most users decided to stay with 3.0, because they couldn't see benefits of moving to 3.1 and 3.2, and I am willing to bet that same thing will happen with 3.3 soon. Good thing with 3.x is that there is a less incompatibility, and is not very likely that upgrade from 3.0 to 3.2/3.3 will break the website. Problem is that they see no reason to do it. And the numbers are telling exactly that: WordPress has too many major versions that go unused, and having one major release a year would be much better solution: core developers will have more time do work on it, more features would go into it, and there would be bigger awareness about the update, just as it was with WP 3.0. As you can see with current 3.3, it is already a month late, it has only one or two minor features that have appeal to most users (as a developer I love it, but again, developers make 1% of WP users). I know that developers running WP core development don't agree with me, but the wide user base does if you look at numbers from WP 3.0 release until today.

Big problem are versions older than 3.0, how to bring those people to update, and I see no solution for that. This is not a simple problem for many users, since many of them will require to invest into upgrading depending on the plugins they use. I have seen hundreds of WP 2.5/2.6 websites using plugins that barely work, but they depend on it, and they will crash with update. No one will update those plugins for free or help switch to different plugins.