We did this for Caddy 1 too [1]. It was really cool. I am not sure how many people used this feature, so I haven't implemented it for Caddy 2 yet, and in the ~two years that Caddy 2 has been released, I've only had the request once. It's a bit tricky/tedious to do properly, but I'm willing to bring it over to Caddy 2 with a sufficient sponsorship.
[1]: https://github.com/caddyserver/caddy/blob/v1/upgrade.go