A lot of it is lack of awareness of things like Caddy or any other tools that simplify the process. I did not know about it until I googled it right now. I hav

A lot of it is lack of awareness of things like Caddy or any other tools that simplify the process. I did not know about it until I googled it right now. I have spent days/even two weeks figuring out how to set up Nginx and for all I know I did it terribly wrong. I paired it with other tools that I do not even remember. But I would be starting from scratch again if I needed to set another one up. So a lot might come down to that. I was on a team that transitioned from a owned server to cloud as one day one of the test servers went down and after a week of trying, nobody knew how to fix it. We realized at that point that if a server caused a production error, we were utterly screwed as someone who had left set it up and nobody had a clue where to begin fixing it beyond reading endless tutorials and whatever came up in Google searches. The server infrastructure was cobbled together in the first place and for a period was theoretically maintained by people who didn't even know the names of all the parts. At least with cloud, there is an answer of sorts that can be had from the support team.