> where a single update can change or break a ton of seemingly random stuff

That was always the problem with Microsoft: testing was done by the user. But until Win 7 they seem to have released the latest service pack for a given version (2k, XP, 7) with mostly bug fixes. Nowadays in Win 10 and 11 they bundle security updates with features and bugs go unfixed for months, if they ever are fixed. Microsoft organization, from quality perspective, is broken.