Web servers like Caddy automate this for you: you just indicate that you want HTTPS for a particular site and the rest is taken care of for you (in the case of public sites and HTTP-01 challenges, at least). Link: https://caddyserver.com/docs/quick-starts/https
Even Apache2 has mod_md which does pretty much the same thing (sans DNS-01 provider integrations, at least out of the box), so it's going to be good enough for most cases and similarly easy to Caddy. Link: https://httpd.apache.org/docs/2.4/mod/mod_md.html#mdomain
Nginx integrates well with certbot, which does take a bit more work and configuration, but even that is passable: https://certbot.eff.org/
Things can get a bit tricky when you want to run your own CA or ensure mTLS, but in most cases neither will be necessary.
As for whether you even need HTTPS in the first place, I'd say that it won't hurt in most cases and will guard against MitM, the ISP included.