Thanks.
I think the best approach is to just manually update Windows to latest versions on a planned schedule.
Then one can stop the witness node, dumpsnapshot and reboot and then load snapshot and restart in a short amount of time.
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Yeah, it's a challenge to create the multi-boot with Windows pre-installed, but without a doubt, it's the best option. It's just very difficult, and you need to have everything backed up just in case, etc., etc.
Better yet, with older machines that you don't use, a stand alone Ubuntu install!