As far as Windows 2008 is not an officially supported operating system, it would be a bit of adventure using it for live projects.
I have tested Tribon M3 on Win Server 2008 (64 bit) virtual machine running on Hyper-V. Basically it works and shows very good performance, but some functions in the modeling applications are not working - the compatibility is the same as with Windows Vista. If you are going to use it purely as a project and data base server, then I believe it shall be okay.
Regarding licensing - it has nothing to do neither with VMware nor with Windows 2008 server. Just play with the license configuration regardless on what operating system it is running.
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