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.
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.
>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.
The same as where I work (Schwab though for me, not Fidelity). However, they don't track wash sales for me. Do they track wash sales for you? From what I understand, federal law tells brokers to track wash sales for regular stock purchases and sales, but not for stock from vested RSUs, but still requires the stock holder to track wash sales for stock from vested RSUs.
>It doesn't appear like they have to factor in travel into that equation - that's only for your salary.
My employer also doesn't generally track travel for the purposes of taxes. But the state laws say I need to do it and file taxes based on my tracking.
Morgan Stanley at Work seems to track wash sales. Last year I had two vests in May, one week apart. I'd instructed the brokerage to sell some of those shares on vest. On the first date, I experienced a capital loss (less than $20), due to price movement between the RSU vesting and the broker selling the resulting stock. This was reported on the 1099B as a disallowed wash sale due to my acquisition of more stock with the second vest a week later.
I'm just happy that, after years of not doing so, MS started correctly reporting the cost basis of vested RSUs on the 1099. (It should be the same as the amount reported as W-2 income).
I definitely feel the RSU grantors are the customer here, not recipients like you or I.
There is a reason Americans spend staggering amounts of time and money on tax preparation. It is simple until it isn’t.