I added the tls subdirective to the Jellyfin config to no avail
The WX site has always been solid as a rock. The backend is actually Caddy 1 on a Raspberry Pi 4. Accessed locally (http://192.168.0.180), it was served without CSS as well because I think the software (weewx) hardcodes the domain into some of the links to stylesheets.
I think I need to start smaller maybe and switch the WX site on the Pi to Caddy 2 (because its config is very very simple). I tried, but I ended up just getting a blank page with no files being served.
I posted that information in another topic to keep this one relevant.