When you install and configure a server operating system, you hope you'll never have to do it again. It's inordinately complex and time-consuming. Each server is a unique creation, and each configuration meticulously adapted to a particular use.
Any installed drivers, applications and other software components reflect that specialized use. Even individual applications may have a unique set of patches. It's difficult, if not impossible, to identify each unique configuration and determine how to replicate it on a new OS.
So why should you bother with Windows Server 2008? You'll still have to replicate your server environment on each server as you replace your old OS. It should take less time, though, with Windows Server 2008. And when you're done, you'll have a more secure, more manageable and better performing box, both physically and virtually.
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