Considerations
Since the tax rate for short-term gains is significantly higher than for long-term gains (up to 35% versus 15%), it's often wise to realize losses on lots before they become long-term holdings, thereby lowering your short-term gains. In contrast, you should wait for a winning position to become a long-term holding before selling, in order to take advantage of the lower tax rate. The tax savings could be significant. Keep an edge year-round by monitoring both your realized and unrealized positions. In your portfolio, look at the 'Unrealized Views' to identify security lots that are short-term or long-term and to get a count of how many days before short-term lots will become long-term.