Get your taxes done using TurboTax

If you have every transaction listed on your 1099-B entry, do not enter an amount on the Personal Items Sales screen.   You only need to enter an amount there if you are not including some of the sales on your 1099-B entry.    See my example below.   

You only need to enter the amount for proceeds not entered on the 1099-B entry.   If I had not entered the detail of Sale D on the 1099-B, I would need to enter $200 in the Personal Items Sales box.   Whatever is in that box is ignored on the 1099-B entry screen.