I recenty talked with a co-worker. He, like myself, travels several days a work week (if not every day). Older and more experienced than myself, I asked him how he kept on top of his bills. His answer...
Have everything charged automatically to his credit card or ACH'd from his checking account.
Frankly, I was impressed with the simplicity, but concerned that he lost his negotiating position for bills he disagreed with. He makes north of $450k, so I expect cash flow is not likely an issue.
I've began thinking more and more about automating payment for repeating bills onto my credit card. Why not? The card's limit would exceed the monthly bills and certainly simplify monthly bill payments.
Here's the question? Do I weaken my position if I have a dispute? Is the simplicity worth the risk?