I love the latest and greatest: Windows Server 2008 R2, Windows 7, Exchange 2010, SharePoint 2010, and the list goes on. My recommendation is to upgrade everything you have.

At least, it used to be. Now I'm not so sure. This week, I had the strangest real-world question posed my way by Jim Basa, senior network administrator for Lutheran Social Services of Minnesota. He has roughly 50 servers in multiple locations and is considering moving everything to Windows Server 2008 R2 to take advantage of the many benefits. He wanted to know if he should upgrade the Active Directory first and worry about domain controllers, or implement Windows Server 2008 R2 member servers first to take advantage of the new R2 features -- a reasonable question.

[ Read J. Peter Bruzzese's insight into Windows Server 2008 R2 in "Windows Server 2008 R2 polishes up an already sleek server OS," "Criticisms and kudos for the Active Directory Recycle Bin," and "Thumbs-up, thumbs-down: Windows Server 2008 R2 Active Directory." ]

My response caught me completely off-guard. LSS is the largest social service organization in Minnesota, with more than 2,200 employees. Considering its nonprofit status and the fact that this has been a tough economy, I couldn't help but wonder if upgrading every server was necessary or even worthwhile. So I asked Jim what features he was especially interested in using. Here are some of the features he liked, along with some of the ones I personally see as valuable: