I always want to pay my bills on time. In the olden days I wrote checks and mailed them. I thought I was smart because I'd hold the mail until closer to the due date and then post them. Except one time I forgot to mail a check to Visa. I was able to go to the grocery store business desk and pay without missing the due date. Phew! Never again. I already had direct deposit for my payroll (I was one of the last at my company to sign up for that), so then I signed up for everything that I could possibly pay "automatically"... utility bills, credit card bills, etc. This saved me the stress of having to remember to perform these tasks, and when.
Since that time, around 1990, I have never had a problem with such direct automatic payments. I know that many people worry over this sort of thing. But really I have never had a problem with it, and the relief from the worry of having to remember, and to sit down and write out payments, has meant a lot to me.
In the modern world where everything is done "on line" we can pay these bills "on line" very easily. But I still prefer the "automatic" bill payments because I don't want to think about these. With "bill pay" I would still have to remember to log into my bank and take action to make these payments. Not convenient for me.
I will comment that I keep a "checkbook register" in a computer spreadsheet and I actually plot out all "expected" transactions for the following 12 months (my system is pretty easy and semiautomated for me to update). When a transaction changes from "expected" to "actual" I simply check it off my in spreadsheet. This is the method I use to keep track of those automatic payments, I review them and the actual bank draw very closely. I also seem to be one of the few people these days who (1) actually keeps a check register (mine is electronic) and (2) reconciles their checking account with the bank statement each month.
My financial planning/recording/reconciling system is as automated and idiot-proof as I can make it (I am the idiot in this equation). Especially as I start rolling into my twilight years where my mental faculties are "more frail" than they used to be. I can still apply the concentration to build my "systems" and then I just go along without stressing out and having to really give things much thought on the detailed level.