Well, on the virtual machine (guest) side of things, there's no reason you can't keep your Win 7 VM and also have a Win 10 one. If you're planning on using an "upgrade" license, make sure to back up the Win7 VM first and keep it somewhere safe. That way you can always run that one too later.
As far as the host software, just install the trial of the latest version 11.1.x before purchasing the upgrade, to verify that it works with your hardware. Make sure before you uninstall the current version that you have your license info written down, in case you need to revert to this current 8.x version!
