This is another question that came up many times during TechEd.
It was usually phrased, "Why would I go with Windows Server 2008 over Windows Server 2003 when deploying my Exchange Server 2007 environment next month?" Sometimes they also threw in that they were going to to CCR.
My point, which actually seemed to please some of the people is that we, as administrators, should try to avoid NT 4.0 situations that we are still paying for today.
What does that mean? Well, think about it, in 2000, we were deploying new servers. The options were to deploy NT 4.0 or Windows 2000. Windows 2000 was still new and there was fear about using it for critical environments. So, NT 4.0 was used. In 2003, the hardware reached the end of its warranty. So, we paid for an extended warranty for a year, or more, until it got too costly. So, last year, we had an OS that was 11 years old running critical systems.
Take it forward today. I deploy a new and extremely critical email environment that is supposed to last me between 4 to 5 years. So, if I use Windows Server 2003, I will find myself running Windows Server 2003 in 2013. Sound familiar?
I am willing to bet you money that not a single person will be wanting to upgrade the OS to Windows Server 2008 when the application and the OS are still working properly. We, as IT people, do not mess with what is working. So, we don’t upgrade and we end up in a bad position where we are way past the end of life on the operating system on a critical server environment. This is especially true if we are deploying a high availability environment to support the application. You don’t mess with it.
I am a big proponent of aligning application and hardware refreshes because it just makes sense. What we end up with is a cycle of every 3-5 years, we replace our out of warranty equipment with new equipment running the latest OS and the latest application version just so that when we hit the end of our planned life cycle, we are not in an unsupported state and trying to remember how to manage an OS and an application that we haven’t touched in years because we are constantly moving forward.
Something else to consider. Let’s say it is the year 2010, and you call Microsoft for support for your Windows Server 2003 environment. Who do you think you will get to help you? Well, the very best people have already moved on to the other teams. They are working on the 2008 platform, or they are working on Win 7 (whatever its real name will be then). The best support guys will not be stuck working on the 2003 team.
I hope that is enough reason for you to do your best to convince management that it is better to go with Windows Server 2008.