How to move Topics in Category into their own Pinned Topic inside new Categories?

Thank you for the questions, @HAWK. I put together a flow chart to define the logic. It includes 3 entry points into the Discourse forum:

  1. Free trial: Access to Module 0 and Module 1 (Group: Free Trial). No payment needed. Handled via PMP + Wordpress, with SSO. Is subscribed to Active Campaign email series. Removed from email series if/when they purchase.
  2. Paid Member: Access all modules (Group: Paid Member). Payment on WP page via PMP form (Stripe). Add to 15-week Active Campaign email sequence. Removed from Discourse (Suspended?) after 15 weeks if no new subscription.
  3. Alumni: For Paid Members, to stay active. Added to Group: Alumni. Monthly recurring fee, plus Active Campaign email sequence.

I’m open to hiring for custom development, though I don’t want to hire without knowing what I want.

Integrating PMP is relatively straightforward with this link: Manage group membership in Discourse with WP Discourse SSO

I’ve had issues using the new Discourse Subscription plugin, which I’m sure will be resolved. Therefore, I don’t have much experience with Discourse Subscriptions yet.

Here’s the flow chart.

Nope. You can add/remove users to groups as you like.
I understand I can add to multiple groups at once, but can I change group status on an interval? For example:

  • Day of purchase: Add to Group_1
  • +14 days: Add to Group_2
  • +14 days: Add to Group_3
  • +14 days: Add to Group_4
  • +14 days: Add to Group_5
  • +14 days: Add to Group_6
  • +14 days: Add to Group_7

My sense is that I could only do this type of “drip” with a Wordpress membership plugin (PMP, Wishlist Member, MemberMouse, etc).

That depends on how you manage lessons and notifications in Discourse. If a new lesson is added to a category which you have all members watching then they will get an email notification.

My intention is for all lessons to be published, then control the lessons (Categories) that the user can view depending on their payment status and time since payment (drip). No new lesson would be added to a category.

Thank you again for your guidance. I feel like I’m close to understanding the solution. Executing on the solution is another project all together, I’m sure!