I've heard of examples of auto billpay breaking down. I think it can be a great system for some, but it could be disastrous for me, because I think I'd get lazy about checking and confirming that this that and the other happened by the due dates. The only thing that works for me consistently (and this is because I'm a poster child for adult ADHD) is paying before the due date, so that the balance reports as $0. That gives me some wiggle room.
I do have auto billpay on a few accounts, as part of a belt-and-suspenders strategy. It spooks me to think of it as my primary tactic for CC management.
Oh, and I do have things like insurance, mortgage, auto loan, etc. drafted. These are fixed monthly expenses, falling due on the same date each month. I'm happy to have them vacuumed out of my account! Feels different for changeable balances like CCs though.
btw, OP, I'm throwing this out here as part of a general discussion on the merits and weaknesses of automated payments, not as a comment on your situation. I think that's been beaten to death by now. 
edit: Well, poo. This thing used to be animated. One of these days I'll figure out/ remember how to post animations. 
How about this?
First, IMHO, if a bank can debit your account on a Saturday, Sunday, or holiday, then they should equally be able to credit your account on a Saturday, Sunday, or holiday. The transaction is date and time stamped and that's the date and time that SHOULD count.
I prefer to use my bank's online bill pay for all my bill payments. One, easier to manage. One username, one password, ALL my accounts in ONE place. Two, less chances for identity theft as I'm not entering payment inforamtion on multiple websites. Three, payment scheduled date, date funds debited, date funds transferred, date funds recieved and confirmation number all available in ONE place. Most payments are made via overnight electronic payments. Some creditors do no participate in the bill pay and an actual check must be mailed.
Will I set up repeating auto payments, most likely no. My mom did this with her mortgage payment (largest monthly bill). The bank glitched and withdrew the payment twice. My mom caught it and called to let the bank know what happened and get the second debit credited to her account. The $2100 for both payments were on put "hold" and she did not have access to that money. The bank cancelled the bill payments and the payment was actually never recieved. She still needed to make her mortgage payment, fortunately she had reserves to do so. Took 3 and 1/2 weeks for the bank to "release" the funds. They claimed they could not release the funds to my mom because the transactions had already been processed and her account was debited. Even the though the bank cancelled the bill payments they couldn't confirm the Mortgage Co had not in fact received the payments and needed to wait to make sure the money had not really gone anywhere. Now the Mortgage Co confirmed payment was never recieved but that wasn't good enough for the bank. Nope, 3 and 1/2 weeks to get access to money that never really went anywhere. In this day and age of INSTANTLY VIRTUAL information, none of that should've been necessary.
My own bill pay horror story happened last month, with CHASE online bill pay. My cc payment was due on 6/3. I scheduled my payment on 5/23. The payment was to be sent electronically overnight. The payment was funded and processed on 5/25 per my online bill pay. The morning of 6/3 (cc payment due date), Chase sends me a message (not an email message, but the online secure message center you only see when logged into your account) that stated that an account had changed it's bill pay processing time. I open the message to find that the cc account I scheduled a payment for on 5/23 no longer accepted electronic overnight payments and now required 3 days to mail an actual check. As the payment was due that day I got worried and called Chase. I explained what happend to the CSR and asked her to confirm whether the payment was sent electronically or not. CSR stated the payment had processed electronically and went through as scheduled and it was next month that I needed to worry about the new processing times. I thanked her and hung up. On 6/4 I received an actual email from Chase stating that due to an error some online bill payments were not processed electronically and they were attempting to contact the creditors to try and make sure Chase customers were not hit with late fees. Email stated if a company did charge a late fee, Chase would be responsible for the fee. I log onto the CC account website to see if the payment had posted. I could not even get to the acount overview screen becasue it was prompting me to make my "overdue payment" as payment had not been recieved by the payment date. The payment was not received until 6/9. No late fee was charged. However, additional interest was charged and when the account reported it showed a higher balance than the previous month due to interest (only $9) and the fact no payment had been recieved. The CC company reported the account before the errors were fixed regarding the payment. Now I'm stuck with the wrong account balance reporting until the CC updates next month.
No matter how you pay your bills, auto payments, online bill pay, online account website, check, or cash and no matter how diligent you and who you talke to mistakes can still happen. The banks and credit companies have the ability to be more cooperative and make banking more convienent for their customers, they simply refuse to majority of the time. In the electronic data age we live in, these kinds of issues should not occur, and if they do, should be remedied without hassle.
