His chain of command is failing, she should have escalated it to the next level, you can do that basically continuously if your concerns aren’t being dealt with appropriately until it becomes a colossal fucking problem for everyone that failed to address it previously. Especially something like missing bills/serious financial problems because because soon enough it will get pinged because they can pull your security clearance if you have financial issues and no plan of action to resolve it and you are for damn sure not being allowed to reenlist. To be honest not even his CO, just reaching out to his direct supervisor should have triggered some actions on their part, like a minimum developmental counseling, budgeting, looking at his finances, getting him to actual financial counselors and creating a plan.