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Which structure, and when

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Income

Covered call or cash-secured put?

Covered call vs Cash-secured put
Rule of thumbAlready own the shares? Sell the call. Want to own them at a lower price? Sell the put. Choose by what you hold, not by which premium looks bigger.
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Income

Credit or debit spread?

Credit spread vs Debit spread
Rule of thumbIV Rank high (50 or more)? Sell the credit spread and let the rich premium decay. IV Rank low (30 or less)? Buy the debit spread while options are cheap. In between, the edge is small: size down or wait.
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Income

Assigned on a put. Now what?

Calls at your basis vs Calls below basis
Rule of thumbSell calls at or above your adjusted basis: the strike less every premium collected. If that call pays almost nothing, go further out in time, not lower in strike. Go below basis only when you have decided you want out.
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Risk repair

Collar or protective put?

Collar vs Protective put
Rule of thumbExpect a strong trend up? Use a protective put: pay for the floor and keep the upside. Expect chop or a slow grind? Use a collar: let the call pay for the put.
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Defence

Strangle tested on one side: roll or close?

Roll vs Close
Rule of thumbSet the stop before you sell: close at a loss of about 2× the credit. Before that, roll the untested side closer for credit, and roll out in time only for a net credit. Never roll just to avoid taking a loss.
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