Thanks for the section 3 tip, that’s great.

In my case adjusting estimated tax payments on S-corporation profit distributions wouldn’t work because I’m trying to maximize Roth 401k contributions (elective deferrals). Such contributions can only be done through payroll, which excludes profit distributions, and being paid from net after-tax wages are impacted by unnecessary withholding.

If you’re paying FICA on your 2% shareholder health insurance you’re doing it wrong. From S-Corporation Compensation: “However, these additional wages are not subject to Social Security, or Medicare (FICA), or Unemployment (FUTA) taxes”

I don’t see what “reasonable compensation” has to do with the question.

Gaming the system? I’m paying every cent of tax owed, this isn’t a tax evasion scheme. I just don’t want to overpay withheld taxes. No business owner should.