Assuming a process won't fail or a machine won't reboot for 3+ days is a bad idea on any OS, although it's certainly a worse idea on one that's targeted at the general public who only use Chrome and Office.

Writing the code in a way that can't be resumed is the person's second mistake.

Given this anecdote, I still prefer auto-updating Windows because it keeps everyone more safe. It's terrifying that there are millions of machines running Windows with access to my personal financial and medical data, and many of those may have 0-days on them. I don't know how we got by when those devices sometimes weren't fully updated for yeads.