(sorry to be a dummy...) if you have time, please do give an example scenario on how a LEAP CC can fail (ie if cc760 and closing is 755 OTM, the loss is because the LEAP became expensive?)
TIA!
not-advice
The way I think about this the price of the leap, buy and then sell, drives the overall profitability. The numbers tend to be bigger to a lot bigger in these changes.
One example of a leap cc failiing - buy the leap when shares are 920ish, shares trade down to 720ish, and you're selling say 800 strike cc's (low premium; ask me how I know
). The share price reverses fast enough that the 800cc goes ITM and deeply enough ITM that you're stuck. You get to take assignment on the 800 strike cc while selling the leap purchased around 920 for a share price around 800. That probably translates into a roughly $80 loss on the leap to match up with the collection of credits from the cc's.
Another source of loss is that leaps are also affected by IV. If you bought the leap at a relatively high IV and now its a relatively low IV, then you've also got a loss due to the change in IV.
When the leap is no longer a leap and is instead reasonably low DTE and its strike is too close to the money you can easily get into a situation where the low DTE short call delta is higher than the leap delta. That'll mean that each $ going against the short call creates a larger loss than the gain on the leap.
I mitigate all of that by using really long DTE calls that are also DITM. That currently means June '24 500 strike calls. I want these to behave as much like shares as possible, so I want these to be really high delta (.90+ is a number that I like) and max distance to expiration. When the Jan '25 leaps become available then I'll choose a new DITM strike and those will be any new leap purchased from there on.
I've tried short DTE long calls and closer to the money - I get great leverage but if the share price trades down from when I purchased the call, then I can easily find myself in a position with a high delta short call (approaching 1.0) and a low delta long call (2 or 3 months to expiration, share price near the leap strike; probably a .5 or .6 delta. In this situation I see no good choice other than taking the loss and ending the pain. Each $ move down will push the short call deeper ITM and increase the overall loss in the position faster than the leap is gaining value.
I've discovered that I get additional "leverage" by using shares as backing. I put that in quotes as it isn't really leverage - I don't use margin or spreads. The "leverage" comes from selling calls that are much closer to the money than I would otherwise use. A recent example - selling the 690 strike cc against shares I purchased at 703. That position started $13 ITM and opened for about $25. Held to expiration the max gain was $12 - max gain was every share price above $690.
By using shares as backing the net of the shares minus the short call strike is always improving as the share price goes up. The deeper ITM the position goes, the slower the net gain, but its always positive.
In this example (buy shares 700, sell 690 strike cc with $12 extrinsic value) I get equivalent leverage to selling 2x farther OTM cc's against 2 leaps (given that I sell further OTM cc's with a $6.50 credit). From practice doing both I like the aggressive cc using shares over further OTM using leaps.
This is how I think about it