Wordpress with Gravity Form quiz checked & Mailchimp notifications

This WordPress works as a place where people takes courses. They complete the course with the Gravity form quiz plugin. I will need to be able to create reminders based on rules. The reminders should be sent with Mailchimp. Examples of rules: When user changes subarea (wordpress user profile field), send X email ID via mailchimp. After new user creation, send him X email ID via mailchimp. If user doesn't log in in X days after first user creation, send him a specific email ID. I can put this rule more than once, like 3, 6, and 10 days reminders. After X days from first login, send him a specific email id, avoid if a specific Gravity Form ID has the quiz approved. After X days from first login, and if he did not approve a specific Gravity form quiz ID, send him a specific email id. After X days, send him a specific email ID, if he has X role and did not approve a specific gravity form quiz id. Budget: 50USD I will only create a milestone of 10usd for starting the project. I will not release final milestone after testing plugin in my WordPress.