I heard from a member of the community that's still on SQL Server 2005 recently. Yes, 2005. That's an old, unsupported version, but they've got some Access/VBA apps that work well and aren't worth investing a lot of development effort in. The person noted that they could only upgrade to 2008 R2 without rewriting code, and they didn't want to move from one unsupported version to another.

I suspect a few of you are in this situation, though it seems many people I know that still run 2005 (or 2000), also have newer versions of SQL Server running. As there is the need, or opportunity, to replace and upgrade instances, they do so.

In this case, it seems there's not good case to upgrade. A change to newer code would be expensive, but also licensing costs have dramatically risen. If the existing hardware were an older 4CPU (licensed), perhaps dual code x 8GB RAM system from, let's say, 2008 ish hardware, that's a quad core machine. While you might be able to run on fewer cores with today's processors, you'd still be looking at a quad core, single CPU as a minimum for licensing and hardware.

There's also the decision of upgrading to 2014 with new code. That could be a significant effort, with resources spent here instead of on new development. Is that worth it? I think it's hard to decide without knowing more.

Is it worth it to upgrade to 2008 R2? I'm not sure. While you get some enhancements, you're still moving to a version that will go out of mainstream support in a year or two. I'd say this isn't worth the cost.

Ultimately I think Microsoft is shooting themselves in the foot a bit with the minimum core requirements and larger licensing costs, without giving customers flexibility. I think Microsoft would be better served by letting customers license the scale they need.