Caddy and Tailscale can at least alleviate many of the issues and all-but make it automatic and painless (though both are more geared for homelab use). I agree nginx and the more standard webservers/services oftentimes don't have good support and require quite frankly too much manual configuration though. There's no excuse in 2026 for not including acme support OOTB with a single checkbox/config value. Plus, I can't believe the default ACME client is a snap (literally WHO wants this?) and not a simple static binary to help adoption/integration.