[vgb2k18]

I bought into Caddy last year for its simplicity. Loved it, from the moment I saw the off-horizontal default page. I switched back to nginx last month because, like you said, I stepped outside of the expected box. Skill issue? Maybe... I transferred my gunvicorn webapp from WAN to LAN. No more dotcom, just 10.x.x.x ip. To say Caddy didn't like it: error messages were non-specific. Community knowledge (ie, stack overflow etc) was lacking. Then nginx.. It worked perfect with almost default config. Skill-issue or Caddy issue, the point is: Caddy is simpler sometimes.