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I think you answered your own question here. If you sell the shares and buy them back cheaper then yes you can make money off of them if the stock returns upwards.
On the flip side you could sell and the stock goes up even more and right after you buy back the stock tanks.
Thus really your strategy is relevant only to the time of purchase. Either way you do it when you buy or sell the stock you are betting its price is going to go one way or the other.
Regarding taxes any stock sold within a year is subject to regular capital gains tax which is your normal tax bracket. Any stocks sold after a year are subject to long term capital gains tax which I believe is either 10 or 15% I don't recall which.
Hope that helps!
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Blain Reinkensmeyer
STTG Staff
stocktradingtogo.com
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