I have been here for a few months and thought i should chip in with some comments. (Am not a coder but i get around)
1. Bug Tracker? For a company which relies on development i do not see a bug tracking application. Please point it out to me if i missed something.
2. Product Road Map with a time line - this is the single most irritating thing ever. How can developers not have a road map when people are paying for the stuff they produce. If your developers can't meet the schedule then fix that problem and not avoid it by not having a timeline. Even opensource projects which are free generally have a timeline. Here you have people paying for stuff wishing and hoping that a feature might be added someday instead of knowing clearly whether it would be added or not.
Note- This need not be a long winding roadmap, just the immediate next few weeks or months should be enough. Simply don't leave the users blind.
3. Documentation for plugins and themes on a proper subsite. Most people read online instead of readme.txt
4. Better Themes. Face it all the themes here really suck for year 2012. If people wanted frameworks on which they can build there are better options. But you cannot advertise great themes when the themes really look like they were designed in 2001. I doubt anyone ever pays you for your themes. And you cannot say they will come when they will come. Have a timeline and work towards it. If you cannot have a timeline then you are not doing a good job developing.
Why not release a theme every two months and the plugins maybe a little slower. People then know what they should look forward to.