Yes and probably. The government requires all banks to question all non-payroll transactions under $100 or so.
If you had one $3 transaction per month you would need a LOE for each transaction. If you had a group of transactions together with nothing in between you might be able to write 1 LOE for that group. You might also be able to group like transactions together if there is a clear pattern. For instance every week if you send $5 to your friend for gas money for carpooling to work. But if it’s kind of random you might not be able to get around it. Your MC will have the best advice for you based on their knowledge of your finances.
The rule of thumb is traceability. If at all possible avoid using cash or apps entirely and use checks/debit/credit cards exclusively. Cash apps are frowned upon in general but, Venmo is one of the better (more accepted) ones.