Web Servers are HARD!
When you first install your own #Webserver on your own #Hardware, everything pretty much goes easy and right. Over time you get more complex with things. Then upgrades start to roll in. Eventually, you make a mistake and nobody notices anything. Because you care about the content on the #Server, you spend time on that, not reading logs and outputs of cron jobs. You miss some things that would have been great to know. Then in what seems like a flash, you are in Murphy's Law territory.
It's stunning how much a person doesn't know about things they know so much about.