The sales on your 1099-B form should be summarized by category, such as category A for short-term basis reported to the IRS, category B for short for term basis not reported to IRS, etc... There are as many as six such categories, but you probably have less than that listed on your Form 1099-B. You can make one entry for the summary total of each category, which should be listed on your 1099 form, so you may need to only make six entries theoretically. If you have sales for which the cost basis is not reported to the IRS (code A and E) you are supposed to enter each sale for those, but you have the option of listing the summary amount and then attaching the Form 1099-R detail to your tax return that you would then mail in.
For the ESPP stock, any ordinary income component would be listed on your W-2 form in box 1, with a note identifying the amount in box 14 typically. You can determine your total gain on all of those by subtracting the cost of the stock from the sales proceeds. You can then subtract the ordinary income portion reported on the W-2 to determine your capital gain. Once you know what the capital gain is, you can subtract that from the sales proceeds to determine the correct cost basis. So, it is possible to enter all the ESPP stocks in one entry and adjust the cost basis to the correct amount in one entry.
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