Conceptually, this is a fairly simple database; I think it would be
practical to use the following plugins (and some tags) to achieve your
goal.
- DataTiddlerPlugin
- FormTiddlerPlugin
- forEachTiddlerPlugin

The first two plugins allow you to define a form for transactions that
would include something like
- PersonName
- Date
- Pledge (Y/n)
- Payment (Y/n)
- Amount
You might also want a form for defining a Person, that might list
their contact information.
And I suggest using YYYY-MM-DD format for dates, making it easier to
sort by date.

You would then use the fET macros to define tiddlers:
- for each person, listing their transactions (so you know if they
have paid)
- for Pledges, listing all the pledges
- for Payments, listing all payments
You might even want to create tiddlers for activity within date
ranges, so you can report on what happened between the org's meetings.

Hopefully, this gives you some ideas.

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