Solved
For example, if I send in a mortgage payment by check on 12/28/15 and it is not actually cashed until 1/3/16, for what year do I claim that as officially "paid"?
It is considered paid on the date you write and mail the check - in order for a given date to be considered the mailing date, you have until midnight local time to put the check in the mailbox. Once the check has been mailed, you have constructively given it up and the expense has been paid for tax purposes.
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