I'm listed as a wordpress.com favorite blog. If I move over to wordpress.org, will I continue to be listed as a favorite with wordpress.com?
You can try by connecting your self-hosted WordPress.org blog to the WordPress.com network using the Jetpack plugin.
If that doesn't work, hosting with WordPress.com VIP definitely will. Your site is still hosted on the WordPress.com network, only you have full access to it, just as if your were hosting on a different web host. It's the best of both worlds. From their website:
The only con with WordPress.com VIP is the cost - but if you can manage that, then it should be perfect for you.