When you consider just how many variables that Microsoft have to account for when they update Windows, and the number of machines they are updating, then IMO it's surprising that more people don't have problems with their updates.
That's not to say that they couldn't do better, but then other Operating Systems suffer with update problems as well.
Sadly users of those don't have anywhere like SysNative that they can come to if they have problems, and have to deal with their update problems themselves, so we don't really have a clear idea of just how prevalent update problems are with say Macs, or Linux.