I don't think this is really achievable currently. So just brainstorming and welcoming ideas! Lets say... All users start in community via usergroup 1 (free) "Subscription A" is purchased and user is then moved to usergroup 2 (which has more features). THIS IS NORMAL FUNCTIONAILITY How can you award "Subscription A" to user based on activity levels? You can set up usergroup promotions to move to usergroup 2 but not award them "Subscription A" for free. Possible solution #1: T