Axreel Strange (names changed to protect the innocent!)makes a cash withdrawal on behalf of a bowling league for 14,076.68 and later(before cutoff) makes another cash withdrawal for 781.21.

Should box c "multiple transactions" be checked?

Yes.

Absolutely. You're going to be reporting the total of the two transactions even though the first transaction was reportable by itself. Since more than one transaction makes up the total, you need to check multiple transacations.

Yes. BSA requires us to aggregate all cash ins and cash outs separately in one business day. If there is more than one transaction, you should check multiple transactions.