Collecting league dues without chasing anybody

A simple payment policy, three reminders, and one visible ledger.

Dues collection is a policy problem disguised as a technology problem. Write the policy first: what is due, when it is due, and what happens if it isn't paid.

Then make the ledger visible. When players can see their own balance, the awkward reminder conversation mostly disappears.

Three automated reminders — at announcement, one week out, and on the deadline — collect the overwhelming majority of what you're owed.