Has anyone used tax software to handle the calculations for an ESPP?

I have. There's a field on my W2 labeled “OTHCMP” (other compensation) for the reported ESPP income, that Turbo Tax Premier never recognizes when I enter the W2 info. But as soon as I enter the details of the ESPP, Turbo Tax notices it matches up, and asks if that's what the OTHCMP is.

With the year-end statement from the brokerage co. showing the sales details, and the emails from my employer showing the purchase details, its pretty easy. Every question Turbo Tax asks is on one or the other of them.

One year I tried to use Tax Cut, and it didn't seem as clear to me on the ESPP. But that could have been because that was my first (and only) time trying Tax Cut.

I don't know about your other question.

-Joe