I read it as:
>I turned off automatic updates after I was waking up in the morning to a ton of lost work more than once a week as a result of automatic updates.
He would go to sleep with his computer left on daily. At least a week it would have restarted on him having expected that the computer would have stayed in the same state that he left it. Not that he would go a whole week without saving his work.
Not the author, but I regularly leave my computer with a debugging session open (because it's 7pm and it's time to go home). If Windows reboots, it sometimes takes hours to reproduce the bug and reach the same breakpoints again.