Given that you purchased shares during the period 2000 - 2008, your ESPP sales are all qualified dispositions. A qualified disposition is one in which the shares are sold at least one year from the purchase date, and at least two years from the offering date (the date the offering period begins). That is why TurboTax inquires about purchase dates and offering dates.
The grant date relates to your former employer's offering period. The offering period has a beginning date and an ending date, and generally on the ending date is when employees purchase shares. However, each company is different, and shares may also be purchased while the offering period is still open. A public company's annual or quarterly financial reports may contain information about a company's ESPP program, and you might research this information online. These reports would be the company's Form 10-K (annual) or Form 10-Q (quarterly).
The reason why TurboTax asks about the market price on the grant date is because your ordinary income part of your ESPP sale is based on the market price on the grant date. Thus, when you enter the market price on the grant date (i.e., the beginning of the offering period), TurboTax will be able to calculate the amount of your ordinary income as well as the correct amount of income tax to assess against that ordinary income.
Commissions are a form of a sales charge. Did you purchase your ESPP shares through a brokerage firm? If you did, then your brokerage statement should contain your sales commissions. However, if you did not, or don't remember, your former employer's financial statements may contain information about commissions. If you can get this information from your company, then you will have an amount to enter, but if not, given the passage of time, then perhaps the only option available is to leave the commission field blank.
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