Windows 2008 vs 2012

What's the anticipated lifespan of your service/server?
Windows Server 2008 R2 - end of extended support January 2020. (A little more than 3 years away)
Windows Server 2012 R2 - end of extended support January 2023.
https://support.microsoft.com/en-us/lifecycle?c2=1163

Mainstream support for Windows server 2008R2 has already ended on 1/13/2015. Extended support will end on 1/14/2020.

For SQL this is 7/8/2014 and 7/9/2019.

The choice seems obvious If you're setting up a new server?

We have dumped most all Server 2008 (a couple of non-DC/AD servers left) and moved to Server 2012R2 all around.

There is no point (in my opinion) sticking with Server 2008. Server 2012 is not that much harder to learn.

And if you don't lie the interface, there is always Classic Shell

It is a server so I do not worry about things that consumers might use (although everyone may have their own preferences).

I do add a start menu as I do on all post Windows 7 systems (already included in the OS)

Right Click on the Taskbar
Select Toolbar, New Toolbar
Add the following content in the space provided:
C:\ProgramData\Microsoft\Windows\Start Menu\Programs
Save the toolbar. It should call itself Programs.

Personally, I'd like to stick with 2008 R2, but I need RDS CALs (which are NOT compatible between versions) and how long will 2008 R2 stay on Microsoft "life support"?  -OR- Am I totally overthinking on this one?

So you want to stick with 6 year old technology?  In technology terms it's old.  2016 is going to be released in less than 5 weeks...

Staying with 2008 is not a wise decision in my opinion.

Further, you're incorrect about the RDS CALs.  They cover the version they are sold for and earlier versions.  You may need to contact Microsoft to downgrade them, but they are downgradable.

Obviously, everyone agrees, so I guess I need to give an "assisted solution" to everyone who responded!  On a personal note, Microsoft really annoys me with all their releases....I would love to recharge my clients the full price of my software every 2 to 3 years, using calendar years in the software name (brilliant!).  I do see the advantages of keeping up with current technology provided each "new release" actually provides additional value/functionality.  On the other hand, for an application such as my own, that performs perfectly well on their "2008" version, why should I need to keep paying Microsoft for a new version every 4 years when they throw in some changed (hopefully improved) functionality while the version I'm running works perfectly well....just my own "pet peeve" especially with their personal OS versions (7 vs. 8 vs. 8.1 vs. 10)...why?  Anyhow, I've just recently been informed that the corporation that's using my software already has a strong commitment to AWS, so all of my recent research is essentially for "naught" since I'll be dealing with Amazon and whatever servers and remote access they provide.  I do still want to thank everyone for their comments and, if it weren't for the Amazon connection, I would have taken most everyone's advice and would have gone with Server 2012 (2016 is just a little too new for my tastes...).  Thanks!

You don't have to upgrade if what you use runs perfectly well on 2008. You just won't be able to get MS to provide any kind of support if things go boom because the OS borks itself once the version of Windows server you use is older than 10 years of age. But if the new version of windows has a new feature that saves you money, it's usually worth it to upgrade.

FYI: AWS is a more or less cloud-based VM solution. I haven't worked with it yet, but I believe they offer the option of creating VMs that utilize Windows Server on the back end to run whatever applications you want.

Microsoft does not require you to upgrade with every new release.  But there comes a point that supporting older products cost too much.  Technology advances.  PERIOD.  Microsoft provides generally 5 years of main stream support and 5 more of extended support - a total of 10 years.  That's a LONG time in technology.

As a developer (it sounds like you are), you should be part of the Microsoft Developer Network (MSDN) which potentially provides all their software to you for an fairly low and reasonable (considering what you get and what you do, in my opinion) annual fee.  As an amateur developer myself and an IT Pro otherwise, it irritates me when companies don't provide their product on the newest versions of Windows, especially considering that the pre-release versions of Windows are all available with MSDN for many months and occasionally years before release - developers should be building and testing on CURRENT platforms.

In my opinion.

I thought I had already closed this question.  Apparently not.  My prior comment was supposed to be my closing comment!