"if the 1099 isn't negative (income recognized on my W2), doesn't that double tax on the ($15k) W2 income as well as the (positive) income on the 1099? "
You have to understand that the sale of the stock is a completely separate, a completely independent transaction, except that the compensation helps set the basis. Having set the basis you're going to have a gain if the selling price is higher than the basis and you're going to have a loss is the selling price is lower. And that's all there is to it. The "double tax" issue is COMPLETELY ELIMINATED if you use the CORRECT BASIS.
So you said you spent $3K to exercise and the exercise created $15K of compensation, so the total basis for that GROSS number of shares in the grant - we'll call that "X" - is $18K. So your per share basis is $18K/X. What is that number? What was the per share selling price?
