Are you using autosale? It sounds like you’re manually selling, perhaps that is why it’s so complicated. I used autosale while I worked at Google and had no problems

I used to use autosale back when it existed. Now it no longer exists, and has been replaced by an ETP program.

It's been a while since I used autosale, but I think the problem still existed then, because I think even with autosale the sale price wasn't identical to the vest price, so there were still loss sales, which could be washed. But I think since the sale happened the same day as the vest, the problem wasn't as bad, because in 31-day months, the loss sale couldn't be washed by the next month vest. So there wasn't the case of constantly increasing complexity, because the complexity would reset in 31-day months.

I tried ETP back when it was introduced. I didn't like it. It's been a while, so my memory of why I didn't like it is a little foggy. For one thing, when you're enrolled, you're not allowed to buy or sell any Google shares manually. One of the biggest problems was that there's a cooling off period, and the shares that vest during that period don't get autosold right away, and you can't sell them manually. I think they get autosold a month or so after vesting. My memory might be wrong, but I think that's what happened. Another thing that annoyed me is that my sells got split across 2 1099-Bs: the 1099-B from my individual Schwab account and the 1099-B from my EAC Schwab account. I think shares that vested during the cooling off period went on one 1099-B and the shares that vested during other times went on the other 1099-B. And somehow in the confusion I ended up with some shares that never got sold at all.

Sounds way more complicated these days! That’s too bad, I would expect Google to do a better job