Yes. The _Click System Data View is a record of all clicks by Subscriber. You could write a Query Activity to write to a sendable Data Extension and use that as a target audience for a User-Initiated Email Send. All of that can be automated in Automation Studio.

Yes. The _Click System Data View is a record of all clicks by Send Job and Subscriber. You could write a Query Activity to write to a sendable Data Extension and use that as a target audience for a User-Initiated Email Send. All of that can be automated in Automation Studio.