Finally got Community Server 2008 installed
That was a long time coming, and because of that the upgrade path from CS 2.1 was not smooth. But... it worked and my blog lived to tell the tale.
I waited so long because I have a custom module that was not compatible with 2007 OR 2008. But thanks to Timothy Humphrey and his hard work on an updated version of his Subdomain Module I could keep my robbie.robnrob.com direct to my blog setup.
I will post more once I figure out how to wire Ping.fm up to Blog posting against the Community Server REST API.
;)