For TLS I am looking into using CertBot and it appears there’s a module (https://github.com/desec-io/certbot-dns-desec) I can use that works for https://desec.io/ to handle my certs.
You can consider using lego-acme as well. It’s not too different, just that it comes prepackaged with a bunch of DNS providers including desec, so you don’t need to install an additional module.
Since Caddy is handling my certs automatically, how often would I want to renew my certs?
By default, certs are valid for 90 days so you’d wanna renew a bit earlier than that. There’s also the option to use 45-day certs or 6-day certs, depending on the profile chosen.
Would I be required to run the same command periodically to renew my cert?
Yes, but it’s better if you automate them, like Caddy did, and both Certbot and lego can do this well. I run lego via a cronjob which checks for the certs’ expiry, and renew it when it passes a certain deadline.
I am looking to hear any suggestions or experiences about different reverse proxies that are preferably free of AI
Not sure I can recommend anything from that list because I’m not familiar with them, but I’ve heard haproxy to be very performant.
You can use
caddy reload -c /path/to/Caddyfileto reload the config midway through