It seems I finally got somebody competent on the phone. I called the claims department to add the transactions that have finished pending to my claim and also make sure they saw the scan of the check. The lady assured me I'd be getting all my money back, including the insufficient fund fees, and actually froze my account (the customer service lady at the physical bank gave me a look as if I had asked her to move a mountain and asked "How am I supposed to do that??" When I asked about freezing the account from any more of these popping up).
Still gonna be keeping an eye out for a new bank or credit union though. Unfortunately I can't afford any that will charge me any monthly fees.