I’d go straight to Windows Server 2012 R2. Windows 2008 is going to be out of support soon (if it isn’t already) so moving stuff to that OS isn’t the best idea. I’d go as current as possible so that when you don’t want to upgrade for another 10 years you aren’t 14 years behind the ball. Also in a few years finding people willing to / know how to support Windows 2008 will start getting harder as everyone wants to support the newer stuff.
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