If a politician raises taxes, and all it does is change the value of a annual withdrawal on your account, I think that pain would be the same, regardless of difficulty of filing.
The pain is estimating and filing 4 times a year.
They simply do not understand the fact that, no, that check is not "free government money" but is instead money that the government took, held onto for free all year, interest free, and then let you have back after you filed the proper forms.
So the suggestions to have people cut checks to the government (quarterly, monthly, annually) is generally made from trying to overcome that viewpoint that too many folks view their tax return as some form of "gift" from the government, and instead get them to recognize just how much tax money is being consumed.
Which individuals? How do you know these people?
Also I don't agree with your perspective on tax withholding. If you don't want your employer to withhold taxes, I think they have to stop withholding taxes. It's a convenient default, in my opinion.
I appreciate transparency like that, but I hate other examples that add additional steps or paperwork to the process.