Choosing which ESPP stocks to sell?
the difference would be taxes...  Lets say you have two lots, one with a 10 dollar gain, and one with a 20 dollar gain.  And lets say you decide to sell one lot this year, and the other lot in 10 years.  AND, lets say that it turns out the stock price is exactly the same in ten years as it is when you sell the first lot. In all likelyhood, you'll have more income, and therefore you are likely to be in a different marginal tax rate.  If you believe that you're more likely to pay more taxes in 10 years, then sell the lot with the higher gain now.  If you believe you're more likely to pay more taxes now, then sell the lot with the lower gain now.