On the Envato blog there's a recent post that covers some of the future of WordPress resulting from some discussions at a recent Future of WordPress panel from the WP Think Tank.
There’s one thing that we can all agree on: the future of WordPress is bright. Outside of this, the ever-passionate WordPress community is a hotbed for debates on where WordPress should go from here. With 22% of websites running on WordPress, a vibrant open-source community, amazing themes and plugins and a developer-friendly mindset, WordPress is stronger today than it has ever been. So what's next?
Their list includes changes touching just about all parts of the application including plenty of UI updates, a continued focus on backwards compatibility a shift towards plugin-driven development. This would allow new features to be installed as plugins when they're ready rather than modifying the core package. There's also some emphasis being put on making it work for "more than just blogging" and push towards more enterprise-level acceptance.