If you need to enter three sales in TurboTax, then you should summarize the purchases associated with those sales into three totals, then make just three investment sale entries in TurboTax. The only way this wouldn't work is if some of the purchases were within one year of the sale date, in which case you would need to enter separate investment sales to capture the short term portion of the sale. Even then, you wouldn't need more than six entries, one for long term and one for short term sales for each sale.