A. There's no right answer to this. It really comes down to your organization's appetite for implementing new OS versions (some companies like to wait for the first service pack to come out before they will deploy an OS) and the features you want.

Server 2008 has a huge number of features that would benefit most companies, such as Windows Server Core, enhancements to Terminal Services, Read-Only Domain Controllers, and Hyper-V. Server 2008 R2 adds more features.

If there are features in Server 2008 you want, I would say go ahead and deploy Server 2008 and then, when Server 2008 R2 ships, adopt it as needed to get the R2 features. It's probably not an all or nothing decision—you can have a mix of Server 2008 and Server 2008 R2.

Make sure you consider 64-bit. Server 2008 R2 is 64-bit only, so if you have 32-bit hardware, your only choice is to run Server 2008 on those boxes. On newer, 64-bit boxes, you can deploy Windows Server 2008 initially (64-bit edition) and then upgrade to Windows Server 2008 R2 or just reinstall.

Related Reading:

Check out hundreds more useful Q&As like this in John Savill's FAQ for Windows. Also, watch instructional videos made by John at ITTV.net.