We have on prem and do all our upgrades by burn the OS and move the data, with the exception of the hypervisor OS (which has a pretty resilient bulk self upgrade built in, and we have a burn-the-OS plan documented for if they do crash). Even system file corruption of a random pet server? New VM and reattach the data disk. Need high availability? Throw F5 or HAProxy at the problem (assuming L7 protocol support).

Both cloud and on prem can work equally when done right. The most important part is to understand that both have different types of cost (human, machine, developer) and to make the right choice based your/your customer's needs and any applicable laws or regulations about data locality. And yeah, sometimes one will be better for someone and not someone else.

Seven figures of cloud engineering can't solve stupid, but neither can seven figures of datacenter. This isn't some Sith/Jedi concept where you have hard definitions of dark and light or good and evil - though sometimes both will see each other as the enemy, and they are in a way competitors.