Quote:
Originally Posted by GBP04
-general long term/short term capital gains question: say I bought a 10 shares of a stock in 2012 (down 20% overall), 10 shares of the same stock in 2014 (up 20% overall) and 10 shares in 2016 (up 20% overall). if I wanted to sell the stock tomorrow, would it matter which 10 shares I sold? as I understand it, selling the 2016 would be least preferable (because I would be paying short term gains). Would there be a difference between selling the 2012 loser vs. the 2014 winner?
Can't comment on the rest since I don't use an accountant or trade options...
But in terms of having multiple holdings of the same stock (lots), you can use the specific lot method to sell the 2012 loser as opposed to the 2016 winner. Most brokers will let you choose the SpecID/Lot method for your holding, which should then prompt you as you are selling and make sure that the paperwork generated by the broker will have the correct tax information. You should also keep good detailed records of your own. If you google stock lot method, you should get tons of resources to read.