Is there any way of removing (or unflagging) all of a user's flags? I have a situation where a privileged user (role that is purchased) can flag content and receive email notifications to comments posted. When the role is expired, I need for them to stop receiving these emails. Is there any way (possibly using rules) to unflag all of the content they have flagged? Or is there another approach I should be taking?
You have to find out the event for expiring the roles, there you can unset the flag programmatically. However with other approach you can also add a check the role of user you are sending email to.

Here goes the steps:


Install rules_conditional module. This module allows to add
extra conditions inside the rules action.
Please check the screen shots. 


Configurations as in following screenshot.


Remember to have the nesting structure as in screenshot.