Caddy's configuration is so simple and straightforward, I love it. For sure a more comfortable experience for simple setups
The pain I've had with it is distributed configuration, i.e. multiple projects that want to config rules. I've been using the JSON API rather than their DSL.
Do you know how I might approach this better?
I like Caddy's integration with Cloudflare for handling SSL and when I originally saw the idea it was promoted as an easy way to have SSL for a homely but I don't use real domains for my internal apps and that is required with Cloudflare.