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We were on the quarter system and most people paid their dues in full the second chapter meeting of each quarter. If you were on a payment plan, you usually had 3 payments in the quarter, beginning with that second chapter and then every 2 weeks. We didn't have many problems, but sisters who weren't up to date on their payments couldn't attend any sorority events until they were. You could even take this up a notch--if it is required to attend chapter meetings and there is any kind of consequence for not attending (a fine, not going to events, whatever), then don't allow sisters who aren't up to date with payments to attend meeting.
With shirts, paraphernalia, etc. it's pretty simple--they don't get the item until they have paid for it. And yes, if they don't pay at the time of order for something that's ordered in advance, don't order their item. They'll learn quickly.
Perhaps you or another exec member should give a little chat to the chapter about how it's not fair to wait to pay until the end--if they want events, they need to pay, you can't do anything without money, whatever.
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