I just watched Dries' State of Drupal talk from the Open Source CMS Summit at Yahoo! in March.

Here's what he discussed (based on my shoddy memory):

Scale - focus on support and security.

Innovations in core.

We've eliminated the webmaster. CCK and Views eliminates the developer. Can we further remove the developer and even eliminate the designer.

Work with web services. OpenID, Amazon S3. Data API.

Critical features Drupal needs to "catch up" on:

- lightweight assest management
- structuring pages in heirarchies
- forum module improvements - learn from other forums, flatforum. Reworking comment system for more flexible handling of data.

Amen to the lightweight asset system. Image + img_assist, IMCE, upload module, ... are all awkward.