To be clear: I'm not asking for opinions, rather I'm looking for data/facts/insights that will help me get closer to forming my own opinion.
We're about to upgrade our servers (as they're old), and our current supplier is proposing to put Windows Server 2016 on the new server.
I've been told that it might be a better idea to keep running on 2008r2, since it's a proven and stable version, as opposed to 2016 which is new. Also, our company isn't that big (50 computers), so we don't need cloud/hybrid stuff that's in 2016.
I've read about Microsoft's Premium Assurance, which allows using 2008r2 beyond its 2020 end-of-life date.
There's also upgrading to 2012r2, which has an end-of-life date of 2023.
Upgrading to 2012r2 seems like the best option, given Microsoft even still allows buying 2012r2 licenses. I'm also wondering about how and if the licensing system is different between 2008r2 and 2012r2.
Can someone provide some insight that will help me make/get closer to a decision?