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I've been using Chromebooks more and more where upgrades are almost transparent. When I go back to my macbook (haven't been on windows for a while), I'm surprised how disruptive upgrades are. I'll trade far fewer OS features for a seamless upgrade experience any day. I wonder if these OS developers realize the UX implications.
I'm in the same boat as you. I use a work Chromebook at home and new MBP with touchbar shudder at work.

I love how "updating" the Chromebook is a simple restart. It's quite literally seconds to be back to where I was previously before the update.

I keep putting off OSX Updates since they can sometimes take 10-30 minutes and the machine becomes unusable during that time.