re: Taxes. How do I minimize the pain?

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I am trading.
Not investing.

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Here is a fairly useful article on Tax loss harvesting


But while trading, as said above, you’re going to be making regular income on the sales, for all intents and purposes. Uncle Sam rewards you in your risk by sharing some of your losses (see above). I understand Robin Hood does a decent job at helping you track this, but you need to keep track of all realized gains/losses.