I’m not sure if you can do it with the plesk plugin, but you should be able to do it with certbot or one of the alternate clients.
Since wordpress is determining what the server sees, then the single cert will need to cover all the domain names, as long as you have less than 100 though that should be fine.
For generating the cert there are a couple of options. You can use webroot and provide a different webroot for each domain or (I think the easier ), just set a redirect for all .well-known/acme-challenge requests to the same place ( in your apache / nginx / other config ) and then you can use a single webroot location.
Once you have the cert, I’d personally just set up a symlink in the storage place that plesk uses for your cert, to where letsencrypt stores the cert ( this may already be done if you used the letsencrypt plugin for plesk).