@joelpomales I've done it many times, find an old w box and let it rip. Nonsense like this is why so many people hate those of us who support open source alternatives to commercial products.
@joelpomales
Try installing a from the box, fresh install for windows, then let it run windows update.
It WILL fail, and your eventlog will be flooded with errors and warning, this is how it's been for the last 2 decades.
Microsoft calls it normal behaviour.
@joelpomales Once for <reasons> I updated a vm from Debian ... to Ubuntu 
... even that went pretty much seamlessly.