Comment by RajT88

Yes, it's complicated because the tax code has been designed for special cases, where there is an opportunity cost to identify and use the special case, but that can be paid for with large enough savings. If hiring that tax preparer/accountant costs $1000 more, but reduces the tax by $1001, then it is economically worthwhile. But in reality, most people are not able to use these provisions and of those who technically can, only a few can use them efficiently.

If you mostly have income from wages, interest, and dividends, your tax is hard to reduce using special provisions and your return is easy to file. If you have a lot of income from business investments, property, minerals, esoteric securities, gambling, etc., then you have more places where you can use these things, and your taxes are accordingly complex.

Yes, the reason is Intuit.

All right, I guess I see your point. If you company doesn't handle the complexity, it can be a nightmare.

Where I've worked, they withhold the necessary number of shares from RSU's and it just gets taxed as W-2 income. Then, it shows up with the taxed cost basis in Fidelity so you don't get double taxed when selling shares. It doesn't appear like they have to factor in travel into that equation - that's only for your salary.

As far as options, it was similar where I was receiving them. The only issue I ever had exercising options was when the company whose stock I was trading changed names, and then the IRS suddenly believed all those options were 0 cost basis and wanted a bunch of money. That took two rounds of letters and a call to HR to get sorted out. Granted - laws have changed since then - that fiasco was 18 years ago.