[quote user="M*_Philip"]....That said, I think either covered calls or cash secured puts are a good way for fundamental long term income investors to generate an income stream. The key is to execute either strategy on stocks that you wouldn't mind holding for the long term at strike prices where you'd be happy to buy the shares.
Again, in the Morningstar framework, write the puts (or covered calls) at a strike near the five star price. If you're income focused, you can also consider what you expect the yield to be if you buy the shares at the strike price (and assuming the dividend won't be cut). Obviously, you'll get the most income if the shares are already below or near the five star price when executing this strategy. You might want to look at the annualized premium measure available on the custom display controls on the options chains.
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I'm hoping that, in the underlined sentence above, the 'five star price' strike target applies to the cash secured puts, and not to the (parenthetical) covered calls.
It seems to me that one could look at a cash-secured put as a limit-buy order that generates income. Similarly, the covered-call is limit-sell order that generates income. Obviously, the analogies are not exact, since limit orders tend to fire when the limit price is reached, whereas puts and calls get assigned when the strike price is reached and (usually) the date is close to expiry.
Nevertheless, I find it helpful to ask myself, "Am I willing to buy (for the put) this stock at this price on the expiry date?" If I can't answer, "Yes," then I need to reconsider the strike, the expiry date, or the underlying stock itself. I can ask a similar question when writing a covered call. But the prices will be different. For the call, I would be willing to sell at the one star price.
To me this seems like swing trading on top of a long-term position — particularly so if you sell the call when the stock is at the two star price and sell the put [buying back the call if you are short there] when the stock is at the four star price. Doesn't work for all stocks, doesn't work all the time, but when it does work, it is sweet.
Finally, I am much less concerned about assignment of calls when I and working inside my IRA, and thus not worried about preserving a long-term capital gains position. In the taxable account, I tend to use roll-outs to avoid assignment of a stock I have owned for a while.