I think it's great for 2.9 to be a media centered release, but how long are you going to wait to get rid of the absolutely horrible page ordering system. I mean, you have "we know it's janky" in the CMS!
I've been using WP for a long time, but c'mon, the page ordering system is pretty awful ;)
You've got jQuery in there, page ordering is already an option, why not just make it drag and drop on the edit batch page screen and then in the single page edit screen have a sidebar item that has all the pages that you can make a mini drag and drop. Just use jQuery UI and make a couple DB calls and we will be golden :)