I’m rather happy with the current path the WP community is following – notable cool things in the upcoming months will include

• create your own post types from within the admin panel (#9674 (Better support for custom post types) – WordPress Trac)
• BuddyPress will become a feature for standard WP.org installations
• Custom taxonomies are becoming progressively easier to implement
• It’s getting progressively easy to work with custom fields.
• There are two WP Google Summer of Code projects dealing with AJAX inline reordering of pages on the manage post screens.

That said, I’m not sure I really need the media handling improvements now the focus of the WP 2.9 development. But I think it’s a generally a good thing. Now if they only allow easy flickr integration or API searching of pictures from the edit screens and improve the internal linking features, I’d have a hard time to find a lot of thigs I still don’t like about WordPress…