If a person has regular, consistent income year-after-year, then it should be easy, IMO, to set up the deductions to take care of that situation without having to file quarterly.
However, if a person has irregular income year-after-year, then there's no way of knowing exactly how much to pay on a quarterly basis or whether to pay anything extra at all.
This is why I don't schedule any "automatic" payments every quarter because I might be paying taxes when no taxes are due. I simply wait until I see how my investments are doing and go from there.
If my investments are producing (taxable) income, then I send in a quarterly payment (approximately) when it's due. I use the EFTPS system for making IRS payments. It's very simple and easy to use once you have it set up.
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