Better WYSIWYG editor
Eh… The current one does suck… But in my opinion all WYSIWYG editors suck.
But I hardcode all my web sites and hate not being able to fully customize my stuff. But that’s because I know how to do that, most don’t.
:-/

Plugin Automation
Eh…
That would be kinda nice I guess…
:-/
Again, I like being able to customize all my stuff. Besides, I bought an FTP uploader, so I need to use it right? ;-)

Better Image Handling
Hm… I disagree here.
I want my blogging platform to focus on blogging. If I want to do something with images, I’ll use that - they’ll do a better job than a web app anyways.
But again, I have Photoshop.
Even so, (like you said) there are many simple free shareware/freeware apps out there that do that.

Built in community features (profiles, messaging, etc)
What you’re asking for is almost completely different than blogging - almost.
Although, check out the Community Version of Movable Type. I actually considered that for a while…
(but note that the installation isn’t as easy as Wordpress)

Integrate with OpenID or Facebook, Digg, something so they can login with their identity and post)
Uh… no.
Sorry, but no.
There already is that feature - entering your URL in the URL section of the comment form. I’m logged into Facebook, Digg, and the others all at the same time and I don’t want my links to go to any of them - I want the links to go to my blog.
:-/

Advanced Image Gallery
Eh…
That would be nice, but again, I’d prefer that the people at Automattic focus on blogging, and not image stuff.
There is 3rd party stuff out there though.
:-)

Built-In Code formatting for posts
Again - I hard code everything, so I wouldn’t need that.

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Nice thoughts!
Now all we can do is wait to see what comes!

Oh, btw, I found this through Entrecard.
:-)