Two examples from my experience upgrading from Caddy 1 to Caddy 2:
Ex.1: Caddy 1 by default bound to an arbitrary port and served via HTTP, they now default to HTTPS, which doesn't work for me since I use traefik in front of it. Bypassing this means adding a ugly ":80" in front of every single vhost I have (which is 20+), before it was just about adding "ssl" if I wanted HTTPS.
Ex.2: The reverse proxy is now transparent by default, in Caddy 1 it wasn't and you just added a "transparent" flag if you wanted it, but now you can't opt out of it and you have to manually specify every header in the config.
I don't think my use-case is that unusual (file server behind edge router) and yet I feel like I have to work against Caddy every so many steps of the way, at one point I will have to ask myself how much more work would it take to just go back to nginx instead.