Thanks so much!
The employer really doesn't know what's going on, just that my W-4 "isn't right." Square just refuses to cut a check, saying they cannot withhold the amount they need to based upon the W-4 numbers. I've tried twice, amending the numbers each time, and it has balked at a paycheck. The IRS calculator I have used to configure a W-4 gave me the answer of "Your tax liability is greater than your income" - essentially no help.
All of the W-4 information I can reference suggests that the system is based on W-2 earnings being the "source" of funds for paying taxes (estimated or otherwise). I usually have to click the boxes in TurboTax for "this is uncommon and doesn't apply to many people" so the territory isn't new.
I should get paid again in a few weeks. We will see if how I filled it out this time works and if they will cut me check. I completed it with numbers that are our "normal" income levels, without those things I know we will do this year that create our need for estimated tax payments.
As long as we have "safe harbored" our taxes, we should be okay, I think.
