Delta neutral can be a misnomer as a position can have different characteristics as it moves. In my position, while I said it is delta neutral when it was first put on, it was acutally leaned long by 1100. One reason was the bullish bias, but most important was where my long premium was situated within the position. The long gamma came from out of the money calls. To compensate for the likely hood of false deltas, I chose an appropriate level which still left me with plenty of profit to the downside. These deltas were factored into my risk/reward scenarios. If the position was truly delta neutral, it most likely would have been slightly more profitable to the downside than up. So, the first place to start with your hedge is to look at whether you will run into similar problems with your position.
Another area people can run into problems with hedging is the comparision between the characteristics of the two. In other words, hedge an option with one that has similar traits. For instance, a poor hedge would be if, in IBM, you sold an Oct 75p, bought a May 95c and sold stock delta neutral. In this scenario, if the stock went down, you would be OK, if the stock went up, you'd be slaughtered. It is an extreme example, but it illustrates a point that the further away in strikes and expirations two options are, the worse the hedge each provides the other. Hedge an option with a like option.
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