Anonymous wrote:I would put his 3 bills on auto-pay, because you don't need the stress.
I'd switch him to cash only - no credit cards or debit cards. $X per week and when it's gone, it's gone. For some people, cash feels like "real" money and cards is funny money.
i put ALL our bills on autopay and set up many alerts when balances run too high or too low. capital one is pretty good for alerts. i also set up automatic savings deductions for 529 and 401k. The only bills that is not on autopay are property taxes and income taxes and a few medical bills (soon to be handled thru HSA account).