Conditional emails to prosite customers

Hi There,

I'm wondering how I can send conditional emails to my pro site customers. For example -

Users on free trial get "X" email. New users of level 1 membership get "Y" email. New users of level 2 membership get "Z" email.

Ideally I'd be able to get all my users with some prosite meta data info into mailchimp. Assuming that this isn't built in, what hooks would you suggest I use to get site url and site "level" into user meta data -> mailchimp, and update it if a customer upgrades or downgrades their account?

I did see in this thread: that the developer was planning on making prosites level information available to enewsletter. Did that actually happen? If so, how do I target site admins based on site level?

Thanks for your help,