In that case the short-term gain rate would apply. But when writing fairly long term out of the money options as I did, I can always buy back the options if the share price gets near too the strike price. It's highly unlikely that the options would be exercised while they are out of the money and far from the expiration date.
So I'm understanding the benefit if the stock drops in price. Namely, you've received $20/share by writing covered call right now so if the stock drops (and you think it'll go back up), then you can just close your covered call positions by buying them back at a much lower price.
However, in the case where the stock rises in the coming weeks/months to $180+, then I'm unclear of what choices would be available to you. I'm guessing if you thought the stock will drop from $180+, then you just hold your covered calls and then close them out if the stock price dropped (and you think it'll recover back to $180+). The other choice would be if you thought the stock would continue to rise from $180, then you could close out your covered calls positions at a loss by buying them (but at a much higher price, ie., $30... so an overall loss of $10/share). Otherwise, I'm guessing you wouldn't want to be holding on to those covered calls in Jan 2014 if/when the stock is $200+ because then they'll get exercised at expiration date and you'll be liable for short-term capital gains tax on your stock gain (from your cost basis, if held less than a year which I'm assuming it would be).
I'm guessing writing covered calls at $165 Jan14 would make sense if you think $200+ stock price in Jan14 is unlikely, and you're more expecting it to be somewhere between $150-180 with possible dips under $150, and you're confident that you can close out your covered calls if necessary with minimal loss prior to Jan 14 if needed. Is that fairly accurate, Curt? Or are you seeing it differently?