Thanks for the response. My Schwab 1099 actually looks to be reporting the dates correctly on the options but backwards on the stock sales. Wells Fargo is showing acquired date after the close/expired date. I don't want to change the dates in turbotax to what I believe to be the correct reporting because then the 1099 the IRS has won't match. Since it is a short sale, I can make sense out of the date reporting. In turbotax, I just don't use the expired button and it seems to work out fine. Even though I have a cost basis on option contracts that were bought back to close the position, the 1099 shows $0 and the amount is actually reflected in the proceeds total. As you stated, since all of these have a holding period less that a year, it is all short-term gains or losses and it should be fine. After all, they just want to make sure they are capturing the correct the tax on the gains.
