@Gregg10 

"Need to have simple functionality that recognizes the original check was outstanding through the void date, and the re-issued check has all the same itemized payables listed on it."

There is an easy solution: create a deposit for the amount of the original check and assign a bank Clearing Account (set one up if you don't have one) and dated as of the date you need to re-issue the check.  Then, re-issue the check and assign the same Clearing Account to the check.  You can post the deposit and check to A/P but, if you do, don't forget to apply the deposit to the check .

That will keep the original check outstanding through the "void" date and not change the effects of the original bill and payment.  Then, the next time you reconcile, clear the old check against the deposit and clear the new check when it actually clears.  Works like a charm.