Do you plan to upgrade to Windows 10 in the next 12 months?
No, if anything, I might either downgrade to Vista or upgrade to Windows Server 2012 R1. If new games don't support 7/8, guess I'll have to have a 10 PC I remote into to play games. Might try to make some sort of VNC that only uses 127.0.0.1 or something.
Are you paying for extended support?
No, I actually usually don't update my system fully anyways, most of my installs are about 4 years out of date update wise.
What is the main reason you haven't upgraded?
Telemetry, bloat, instability, bad design, UWP, and more.
Note: Server 2008 R2 is basically Windows 7
Edit: I've realized that 127.0.0.1 wouldn't work, I'd need to use the network IP of the computer, but that's easy to grab.