Automessage + Pro Sites integration

Automessage is a pretty sweet plugin, but is there a way to integrate it with Pro Sites?

For example, instead of just sending emails on blog creation we should also be able to send emails X days before a free trial ends. E.g. "Your free trial ends in X days, activate a subscription before it runs out" or "Sign up now for a X% discount" in the final message.

For those not using a free trial, we should be able to send a message on blog creation if a subscription is not activated within X days. E.g. "You signed up with us yesterday, but didn't activate an account. Do you have any questions we can help you with?"

A few if/then options that include Pro Sites free trial and subscription statuses would make this already great plugin 10x more useful since the foundation for conditional statements is already there.

Thoughts?