Josh,
I'd be interested in knowing what specific things could be done to make you think that the Web version is no longer the 'ugly stepchild'.
If I consider our (Pivotal's) current development process then the most honest thing we could say is that the desktop application is our afterthought. All of our development is done in the browser, our acceptance environment is an application pushed into a garden container hosted in the cloud.
Admittedly, we haven't focused on the installation experience so if you could explain why it is so painful we could look at merging some of the things we are doing for acceptance into the application itself for distribution.
-- Rob
