If one were to install VMware onto an OS that was being used in VMware, would it be a true test of the new system? That's kind of confusing, so let me try to explain a little better. I have Win 7 Pro as my host OS. I use VMware to run Ubuntu. I do this because I'm not quite ready to make the switch completely. Now, while in Ubuntu, if I were to install a different type of virtualization program, which is supposed to allow Ubuntu to play Windows-based games, would this be a true test of Ubuntu's capabilities to play those games, or would it all be based on Win 7?

I assume your talking about using WINE to run Windows based games?

Games won't run well at all under vmware, even if your running them in a windows virtual machine.

I guess it will test whether or not WINE running on Ubuntu is able to run the games, however from a performance prospective, it will not replicate what you will see if Ubuntu was installed directly onto the hardware.