I've been thinking about covered calls as a strategy recently and there is an important problem with the strategy for me - at least emotionally (only 15 months of doing these to be able to articulate this!). To make these really work well, and this being the Wheel thread and all, I actually need to be ready to take assignment. Not just in theory but also in practice. I don't need to seek out assignment either, but I need to have a much quicker trigger on taking assignment. In particular - each time I consider rolling for credit / strike improvement / time due to being ATM, I need to think seriously about waiting for assignment over rolling.
It turns out that due to my long term buy and hold view on the world, I've got a big problem letting any shares go to assignment, so I wind up with too heavy of a bias to sticking with the short calls and rolling (which has gotten me into perma-roll territory; I don't want to revisit that again, and assignment is a mechanism to avoid that).
But I've also got a few long dated leaps in hand now, and I've discovered that I have no emotional attachment to them. Letting those go due to short call assignment is just fine for me.
I'm working through some questions about how to implement this and am looking feedback from others. Do I go really deeply ITM? How far out in time do I go? How much net time value (purchasing time value up front, getting some of it back when I sell) am I paying for, and how does that translate into the weekly / monthly earnings?
So far I have Jun '23 300 strike calls and Dec '21 500 strike calls. These are sort of the inner and outer bounds of what I think will work for me. The 300 strike was chosen as something I think will still be ITM, even if we get a serious meltdown (return to say the $400 share price). I also chose these for tax reasons - if assignment doesn't happen for 12+ months then I get long term capital gains treatment when I do sell / take assignment.
The $500 strike was chosen as being deep ITM and pretty low time value.
In both cases my intent is to roll / close these calls with 3 months to go - maybe as little as 2 months - but I want to sell them when I can hopefully still get back a lot of the time value I paid for up front.
Assuming I close at 3 months and assuming that the time value then will be the same as a 3 month option is today then the net time value per month goes down as the option gets further out in time. My initial read on this is that I'll go at least 15 months out with a bias towards the 24 month options. As the option gets further and further out, I'll also bias towards lower and lower strikes. Lower and lower strikes due to the obvious risk mitigation - I've got that much bigger of a window to be OTM, so the covered calls can continue. Also as a drag on just how much leverage I'll take on.
Make no mistake about this - using calls to back covered calls is using leverage. That means unrealized losses will accumulate faster than share ownership, just as unrealized gains accumulate faster than share ownership. But a bonus - so far the level of leverage seems to allow for a larger number of covered calls while simultaneously enabling me to stop selling any covered calls against my shares. I find that dynamic very appealing.
I -have- figured out that "assignment" really means taking a short call close to expiration (time value ~0) and then doing a BTC on the short call plus a STC on the long call its covering. That will transition a position from a long call to cash. I could choose to exercise the long dated call when the short call gets assigned, but that early exercise on the long side just means I'm giving back that time value. Thus the STC/BTC instead.