Hi Critter,
Thank you for your help. Appreciate you pointing me in the right direction.
I can answer YES to both (1) and (2). To quantify this a bit: Sum (all bonuses in 2019) = ~1.5*W2 comp.
Now, decomposing this a bit, I did not have enough withheld to cover two extra and unexpected bonuses (Aug 2019, Dec 2019). My deduction situation isn't changing from FY2018 to FY2019, and I did a bit of planning to account for the Jan 2019 bonus. But since I have this extra burden of the Aug and Dec 2019 bonuses, my eventual tax liability is going to far exceed conditions in (2).
I 100% agree with you re: employers paying outside the payroll system. You can guess the reasons why.
Also, suddenly changing the trend and paying two bonuses in the same year for two different performance periods, just so the majority owner can avoid having the firm income show up on their personal income statement for FY2019.....not good.
Having said all this, I am grateful that if I have to deal with financial problems, these are the problems I'm dealing with.
Thanks again.
