[jldugger]

Counterpoint: autopay gives me peace of mind knowing that I won't miss a payment, which has huge downsides: credit score dings, interest charges, and potentially declined charges.

What I think trips people up is accounting for future expenses. The personal finance tools I've checked out focus on historical transactions but fail to put this to use and forecast future transactions. I set up GNUCash[1] to automatically create all the random monthly bills up to 3 months ahead of time, including a guess at CC totals.

I still check monthly, but its mostly just confirming nobody's stolen my card and updating my investments, which I can't forecast ahead of time =)

[1]: https://www.gnucash.org