I have no inside information, but just from perusing the interweb when the question came to mind tells me there may never be an R2 of SBS 2008.
Why do I think this?
- Microsoft has in recent times begun shipping new products more quickly – a la Vista & Windows 7; Server 2008/2008 R2.
- Server 2008 R2 has been out quite a while already. The least they could have done was provide R2 as a license for the member server (I’ve already got 3 installs working this way with separate licensing). Seems pretty silly that a new purchase of SBS Premium doesn’t get you R2 licensing (making SA kind of a must have, even though we’re left guessing).
- Exchange 2010 is out now. Why would they pass up the opportunity to release a NEW SBS product vs. R2 with only a new Server code base.
- Office 2010 is imminent.
- Eric Ligman makes a passing reference to EBS 2010 in THIS POST about the demise of EBS, insinuating EBS 2010 was the NEXT version of that product, which is/was part of the same family as SBS.
So I’m predicting a Fall release of SBS 2010. Which will be cool.
Come on Microsoft – make an announcement. I promise it won’t stop me from selling SBS 2008 (assuming it’s an ‘in-place’ upgrade 
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