All my recurring fixed income expenses are automatically paid from my checking. Variable expenses I schedule myself, because I don’t have a CC, and I won’t give a third party access to my bank account. I check each month to make sure everything went as scheduled though. That’s just me being paranoid.

Jesse W.
http://www.subprimeblogger.com

I’ve found it just relaxing to not worry about certain bills like the mortgage. I tell my bank monthly my mortgage is paid on the 1st, HOA 1st, etc.

Because I’m self-employed and have very uneven cash flows (usually only pay myself two to four times a year), I have my account set up with overdraft protection from its associated savings account, and the savings set up for overdraft protection from a secured line of credit. The line of credit is then set up to have the minimum monthly payment (interest only; current interest rate 4.75% per annum) paid out of the account. You could say it’s all on autopilot.

To guard against identity theft or errors, both bank and credit accounts are set up for unusual transaction and balance alerts, and I check the accounts online at least once a week when I post everything to Quicken.

This way, besides no late fees or interest charges on the credit card or other bills, there’s also no risk of overdraft fees.

I know some people see credit as somehow not real money and for them, this system could be risky, but for me it works. I know pretty exactly where I stand, and the line of credit has to be at zero balance before I will allow myself to spend on anything discretionary. When I do pay myself, after paying off the line of credit and maxing out my IRA contribution, enough goes into the savings to cover my anticipated expenses for the next three months, while anything over that goes into my long-term investment account.

Obviously, I’m not living on the edge; my annual income is usually pretty good, just very uneven. Anyone on a limited income would have to manage their funds more closely. But there’s a lot of peace of mind knowing that if I get super busy at work, go on a trip, or just get lazy and let the bookkeeping slide, I’m not going to get hit with high-interest finance charges, huge overdraft fees and possible interruption of services. The very worst that can happen is a month or two of low interest charges on my line of credit.

I get all my bills online (except rent), pay them all online when I receive them. The only automated thing is my Roth IRA contributions and student loan (because I get a discount)

Waiting until the due date would cause stress I think, but I like to make sure nothing looks out of whack.