You will need to report each sale separately or (if you choose to enter summary entries) you will have to send a copy of your 1099-B to the IRS. TurboTax will print an 8453 for you if this is your choice, and you will attach the copy and mail it. If there are only 10-20 entries, I find it easier to enter them manually.
"Cost Basis" is what you paid for your investment. This information should be on the statement for the period in which you purchased the investment.
