Sudhir has been blogging up a storm lately. He has a series of posts describing what we've done to improve setup for Orcas, and covers some likely "Whidbey to Orcas" migration scenarios. For example, if you have Whidbey with a local SharePoint 2 installation, you might wonder how to upgrade to Orcas and end up with a remote SharePoint 3 deployment. Wonder no more!
It is a LOT of detail to digest, so please keep sending us feedback and questions.
Sudhir also provided a pair of scripts that we use to configure WSS2 and WSS3 after they've been installed, so that they can be used as "existing" SharePoint installs for our testing. I want to make it clear that you do NOT need to make your SharePoint match this configuration exactly; it's just the way we do it. But it's a good way to see what all is configured and which values are most frequently used.
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