Quote from Neutral:
You are probably an experienced options trader, and I am sure it works for you, and hopefully for me some day soon. But my concern was more pedestrian, namely, as a newbie, am I missing anything other than the downside risk in the shares I buy at the strike price for the purpose of delivering them.
Nope, not missing anything if that's all you're looking at
Now, I am assuming that this will happen very close to the expiration. If not, I understand that I need to delta-hedge. I have read that perfect delta hedging is a zero-expectation activity, and the transaction costs, as well as the finite steps, make it negative. Better than having my head handed to me to be sure, but I am not very enthusiastic about delta-hedging as I was earlier. I still have a ton to learn.
If you think it's going to rise closer to expiration, wait until it happens and sell a higher strike. Reality is, we have no clue what will happen on what date. Ever hear of penny wise and pound foolish? The "negative expectation" is far less a problem than the head handing a naked option could hand you. If you don't understand the the trade and you don't know in advance how to manage it, don't do the trade ... or stick to spreads which are a lot safer.
But I suspect that experienced traders make their money from directional bets (including no-direction) as well as spotting price anomalies. Those, and especially spotting options price anomalies are beyond my grasp at the moment. As for gamma-scalping, I need to learn more about it before I can begin to comment on it.
IMO, experience traders make money taking higher probability trades and managing the risk with huge emphasis on the latter. Forget about price anomalies.
So, to me, the take-home message (for trying to make money from selling OTM calls) seems to be: If the price approaches the strike close to the expiration, start buying the underlying according to current delta, and buy the whole 100 shares if the price strikes, and endure the 0.5 delta risk for the remainder of the expiration (say a day or two). Hopefully the shares don't turn around and plunges like a rock right before assignment. If the stock turns around, reverse sell back in the same rate as on the way up. If all goes well, I keep the premium, minus the commissions, and maybe a bit of stock appreciation. If the price approaches the strike early, with many days/weeks left to expiration, try to delta hedge, with a view to minimize losses, but expect to lose some money.
Well, sort of. Delta drops as time passes and rises as price increases. The latter is your larger problem. Right now you're around 20 delta. Buying 100 shares at the strike flips you from -50 delta to + 50 delta and reverses your risk. No problem as long as that's where you want to be.
If you buy shares at 30 or 40 delta, you're raising your break even since at 50 delta (the strike), they'll have a capital gain.
I disagree that you should expect to lose money if the stock approaches the strike early and you try to delta hedge. Losses will occur if you are short delta above the upside breakeven or long delta and it reverses to the downside. If it diddles around in a range, you're going to make money.