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Perhaps install cinnamon in a VM like VirtualBox and let him roam over that first? See how he feels.

I’ve tried this with my dad. The problem is, he never boots up the bum to have a go. He doesn’t really get how there can be more than one OS on his physical machine. So basically we are stuck in a cycle of him not wanting to switch until he’s used to the “new” thing but him never using the new thing.

This is a bit hard to understand for young people, I know :-)

Older people have already spent so much time on learning new stuff that they feel spending even more time to learn something they already know how to do is a waste of time. I'm slowly moving into this category myself. Why do you have to redesign something that works just fine? Just because you want to get paid more is not ok reason.

Lie a bit to him, tell him it's "on the cloud". Kind of true for a rather particular definition of "cloud" :)

I’ve had issues with performance related to Windows update, though the issue is typically space remaining on c for the update (I’ve since bumped my Windows partition up to ~500GB since the macOS one I don’t need a ton so have 500:500 instead of 900:100).

I’d recommend not running VMs when it is being sluggish for Windows Update because the VM is going to feel sluggish too.

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