That you can't delete old To/From entries really bugs me so I searched and found that inside the Checkbook Accounts file is a SQLite database labeled Accounts.db that holds all transaction and user generated entries.
After poking around the database, there is an entries table that holds all the transactions entered into the app, and it looks like Checkbook doesn't store the To/From list separately. My guess is that the app looks up the most recent number of entries a user specifies and populates the field from the table. So the only way to remove old entries is to delete the transaction that contains that entry.
This, of course, is all just a guess from spending a few minutes examining the database. I'm sure it's far more complicated than that, but I am certain that the To/From entries are not stored separate from transactions.
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