Hey Matt - thanks for creating and maintaining Caddy all these years! Like others have said in this thread, it is so easy to set up and maintain that it really does feel like "magic".
In terms of speeding up adoption of Caddy 2, it may be useful to have a list somewhere of the concrete improvements between the two (as I'm sure there are many). A (very) brief look and search around only yielded this article[1] which referenced another link of improvements that now 404s[2].
Another piece of feedback: It’s scary to consider using such a crucial piece of software in production when documentation is referred to as “sort of deprecated” and “slightly outdated.”
That blog post is pretty old. We do have a current upgrade guide here in our docs: https://caddyserver.com/docs/v2-upgrade
We also have a (sort of deprecated) wiki with some (slightly outdated) high-level improvements listed: https://github.com/caddyserver/caddy/wiki/v2:-Improvements