The greater the upgrade lag, the more difficult the upgrade.
I was talking to a systems administrator mate about all the new stuff coming down the pipe in Server 2012 R2 and Windows Azure (which, lets face it, says about 90% of what you need to know about my social conversation skills). Not an avid follower of the tech news, he’d sort of heard about Windows 8.1, but our discussion was the first he’d heard about Server 2012 R2. His comment was that almost everyone he knew was still running Server 2003. That while all the news about Server 2012 R2 and Azure IaaS was interesting, he didn’t see that as something that was going to apply to him until some time in the future.
It wasn’t that he wasn’t interested in this stuff, it’s just that he knew from a pragmatic standpoint that the new stuff was going to be old stuff by the time the organizations that he and the people he worked with got around to adopting it. When he thought about the inevitable update, he’d thought he was going to migrate to 2008 R2 or 2012. That 2012 R2 might be an option actually made him think of holding off longer on pushing for an upgrade off 2003. I told him that if he kept waiting, it was going to get harder and harder to get on the merry-go-round. The greater the upgrade lag, the more difficult the upgrade.
It’s fair to say that organizations hold off on upgrading IT infrastructure for a multitude of reasons. If people upgraded in a timely manner, we wouldn’t see 30%+ of people still using Windows XP. However upgrading to the most recent version gets more difficult the longer it’s left. Going from Server 2003 to Server 2008 is easier than going from Server 2003 to Server 2012.
So although Server 2012 R2 is on the horizon, if your organization is still on Server 2003, you shouldn’t procrastinate and wait for Server 2012 R2. If you do, by the time you’re ready for Server 2012 R2, Server 2015 will have been announced and you’ll consider waiting for that (ad infinitum, ad absurdum).
Finally, keep in mind that just like Windows XP, Server 2003 has an expiration date after which it won’t be supported. If you haven’t started seriously planning to upgrade now, you’ll probably still be talking about upgrading at some point in the future when that expiration occurs.