Windows Server roadmap for future?

Microsoft has had a fairly well established pattern of releasing a new server OS shortly after the release of their desktop OS. Windows 8 has been revealed by Balmer to be slated for 2012, so I imagine we'll see a new server OS in 2012 or 2013 (barring any Vista-style delays). I think you're safe in assuming you'll get something out of it. There's at least one guy who thinks he can give it a more definite date.

As for a roadmap...haven't seen one yet. Based on the recent server releases from Microsoft, I just assume that I"m going to drool over it when it comes :-)

For the server licenses, we've never purchased SA, but then we tend to keep servers in production for a long time and run with a mix of OSes. So we've always managed to roll out new versions of the OS on new hardware.

For CALs, it's been a mixed bag. For the amount of money you're talking about, you have more users than we do, so I don't think our CAL strategy of "sometimes SA, sometimes not" would work for you - too tough to keep track of what you've got.