Our goal is to upgrade a machine from Windows Server (WS) 2008 R2 to WS 2016. For now, we don't want to perform a clean-install to the server OS.
But according to Microsoft documentation, there is no direct path to upgrade from WS 2008 R2 to WS 2016 but we can upgrade from WS 2008 R2 to WS 2012 R2, and then to WS 2016.
Since we are not going to use WS 2012 R2 at all, I was wondering if I can use evaluation versions of WS 2012 R2 and WS 2016 to sequentially upgrade from WS 2008 R2 to 2016, and then buy retail version (of WS 2016) to convert the WS 2016 evaluation to a retail version. Is this possible?