@Chip Bennett - We've discussed that a idea a lot as part of our Widgets team. Justin Sternberg has been thinking about this for a while, and there's even a blog post outlining some of his ideas at: http://webdevstudios.com/2013/08/14/webdevstudios-take-on-a-wordpress-core-widget-ui-refresh/

Its something we're working on, but its not ready for 3.8. We'd love to have you help us out — our next team chat is Monday at 20:00 UTC.