I run Debian on most of my systems and run all of my services in docker (with rare exceptions for node_exporter or stable core tools). My base systems get automatic security upgrades, and then I’ll manually check in every few weeks whenever I feel like it.
My services in docker are version locked to a specific major version (when there’s a tag available) so I can usually re-pull to get minor version updates freely without breaking issues. My few more finnickey services get manual upgrades from me every 6 months or so only.
I usually stick to an OS version for as long as I can, and to that aim I stick to LTS versions with long support windows.
4 major versions in 12mo is…a lot. Especially if those include breaking changes for you. Yikes
That argument only works to explain and support the existence of millionaires and multimillionaires. With millions of dollars you can hire out most menial tasks easily. Especially if you’re still living in a reasonable home.
It falls apart when you reach excessive levels of wealth. Your first few million buys you a lot of time to specialize, but your $101st million buys you less. Even moreso when you get to billions.