From a mathematical standpoint, one method I use to determine the second purchase/short of a swingtrade that is going in my favor is to manually determine the average true range of the stock for the past 10-20 days. While most current systems such as Tradestation already figure this out as a standalone statistic, I like to manually backtest to keep the software honest.
Basically, you subtract the daily high from the daily low to determine the range for the stock. You do this for 10-20 days and take the average of this result. What I like to do is set the 2nd, 3rd, and 4th positions between 60%-100% of this range. So for example, if a stock I'm long currently trades at $25/share and has a average true range of $1, then I would set my next three buy points at say $.70 intervals, $25.70, $26.40, $27.10.
What I'm trying to avoid is getting caught in the normal volatility of the stock that autoexecutes a new buy but has the stock retrace those gains to close below the next buy point. At the same time, I want to avoid getting front run should a pending news item cause an overnight gap that blows through a potential buy point.
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