Entering a 1099-B wouldn't bring up the question "what did you do with the money"? That comes up only with the entry of a 1099-R."
"I cashed out 2500 1099b for 103k..."
That's not particularly clear. What does that really mean in full English sentences?
If you're talking about a sale of some of the stock that was distributed out of the ESOP, that WOULD be a taxable event, but if you're getting that "what did you do with the money" question it sounds like you're trying to enter a 1099-B in the 1099-R interview, And I really don't understand that statement "my former company bought the company stock with it." If YOU sold some stock, which appears to be the case, what's the "former company" doing with the proceeds.
I think it's time to gather up your information and perhaps seek some local professional help where somebody can actually see what you're talking about.
BTW, I entered that 1099-R in my own income tax return and got a tax bump of about $7-8K which seems about right for my tax bracket given $30K of "ordinary" income. Of course I had to guess at the code(s) in Box 7.
