Server 2008...Any caveats?

Summer is update time, as every school IT person knows. These couple of months are when we get as much done as humanly possible when major updates and upgrades won't affect students. While my list of projects is insurmountably long, one thing that I absolutely must do is rebuild the servers at the high school. Our active directory is a mess of neglect (preventive maintenance has simply not been an option due to lack of staffing until now), user profiles aren't replicating correctly, and the terminal servers are low on disk space.

It's time for far more than a tune-up. While we could move to Linux, teachers and students have adapted well to Windows Terminal Services and a largely Windows ecosystem at the high school means that now really isn't the time for a transition. I'd rather focus my training next year on making full use of Google Edu Apps.

That being said, I uncovered some Windows Server 2003 licensing weirdness that meant I couldn't access the install media from Microsoft's eOpen site. Long story short, I needed to pay for a Server 2008 upgrade to properly license the servers and get the media I needed for full reinstalls. While this actually allowed me downgrade rights and the ability to get the 2003 media I wanted originally, my limited experience with 2008 and largely very positive reviews pointed me towards an upgrade.

So next week, 5 servers will be receiving fresh installs of Windows Server 2008. The 2 terminal servers will get the 64-bit version; the AD servers (which also handle print, web, DNS, and DHCP services) and our storage server will get the 32-bit version. I'll be reevaluating our policies, groups, security, profiles, etc., and will be able to take a lot of lessons learned over the last couple of years and implement them all at once.

My question for you, though, is what pitfalls lay ahead? What caveats do you have for me? For those of you who have made the migration, share the good, the bad, and the ugly. Let me know how things are going and share your suggestions and comments.