Hello,
Provided Plesk doesn't override the settings for whatever reason, I would expect creating and renewing the certificate should be highly achieveable through NGINX. When the acme challenge is encountered requests would be served to the temp certbot server.
Very new to NGINX as a Proxy but would expect this to work and allow for autorenewals and instantiation. I do something similar with Varnish and Pound on other setups.
Some notes here about switching, havn't had time to test but will keep looking into it.
How to proxy web apps using nginx? · GitHub
Then I would expect the only issue to be adding webmail.domain.com, mail.domain.com variations to the lets encrypt scripts/templates and it should work well?
Has anyone tried this?