How Often Should a Server be upgraded?

They might be getting at the tail end of the life of that box or it could run for 5 more years. It is all about risk management. Do they have good backup? Is this a low-end box or something like and HP or Dell that is still being warrantied? How long would it take to recover this system if it died unexpectedly? You might want to consider virtualization as the next step for them. It is better to plan a system replacement than to have to do it during a failure.

Good question, and you'll get a lot of different answers.
We aim for 5 years on a server. That can be more, or less, depending on business needs that change, or technologies that change. 
In the past, we've changed based on needs of more resources.
Now, with virtualization, you can pack more 'servers' onto one piece of hardware. We replicate virtual servers to a pair of physical servers, so switching for maintenance, or upgrades isn't as painful as it once was...
If I was you, I'd look at swapping soon, not for the age of the server, but for the fact that 2012 R2 gives some really great Hyper-V virtualization benefits that will help the organization, and you, as the person servicing this. Depending on reliability needs, you might think of a pair of servers to allow for replication.

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