I haven't. I've been reading online that mixing Brew with MacPorts is not recommended and that it's better to stick to one of the two package managers to avoid dependency nightmares
Hm, I'm not sure why it says that. Homebrew does not support any of the plugins in their formula/api/repo.
Here's an open ticket about the plugins on Certbot. There was an old workaround, and there is a new workaround. Depending on what version of homebrew/formula you have, one should work: