not-advice
I've got some buy-writes open right now (purchased shares ~720, sold 700 strike cc for this week expiration; about $16 profit if held to expiration and share price >700 - anywhere above 700).
What I've been finding interesting, and this might be due to using an ITM short call, is that this is probably the position I've had the least worry about in like forever. It takes little energy, if I don't see the share price for hours on end I don't fret. It just doesn't matter. I am noting this as I've previously and intentionally turned the wheel and found that I really didn't like the emotions from doing so. In particular I didn't like turning the shares into cash (call assignment), as I was fretting constantly about whether I'd get the cash back into shares (put assignment) at a positive strike to strike change.
I'm down to around $4 worth of time value remaining. That will all drain away tomorrow and with today's share price in the 730s I probably wait for most of that to go away.
Or alternatively I close this position (btc the short call, stc the shares), and open a new buy-write with a purchase price in the 730s. This time I probably go slightly OTM - say 750 or 760 - for the big credit plus the possibility of strike to strike gains as the shares work their way higher.
A bit of background - I'm using cash that would otherwise be backing cash secured puts for these positions. I am managing them more like csp but much closer to the money as I actively want these to go ITM and stay there, with any level of ITM working for me. This is cash that I mostly or completely don't want to use to buy and hold shares or leaps as I already have all of those that I want (or nearly all that I want).
At these very low share prices, where I see little room for further movement downward, I find I like these buy-writes a lot over csp (which I also like). There's just no way I am selling puts that are within $20 of the share price when I open them. But these buy-writes - its easy for me on these.
At higher share prices or after a big move up I won't be opening these - same logic as why I wouldn't open csp in that situation. I use the same logic for opening these buy-writes as I do for csp (open on a down day, take early profits when available). One big difference - on the buy-write I can get an early close on either a down day (short call goes far OTM) OR on an up day (short call goes deeply enough ITM that the time value drops significantly).
As there is no such thing as a free lunch or free money, should the share price drop far and fast enough, then I'll get the big realized gain from the short call, but then I'll also be far enough away from my purchase price that I won't be able to be as aggressive on the second (and later) round of the call sales. If it goes far enough then I might get "stuck" with relatively expensive shares where I'm waiting for the share price to come back before the big credit short call sales can restart.
At this moment (shares 734), the short call is trading at $39 and was originally opened for $38. If I were to BTC the short call and STC the long shares, then the short call will break even while the shares will gain $15 ($734 - $719). The max theoretical gain for this position was / is $18 with the remaining $3 in the time value left to decay.
If I decided that this was the relatively low point of the share price over the next week (I kind of do), then I close this current position for the $15 gain, and sell new shares at $734. I could go ITM with the 700 strike call for a net $17 time value ($51 contract price minus the $34 ITM). Or I could go for something more like the 750 strike call with a $23 contract price and the possibility of the shares going to >750 and achieving the max gain of $39.
The first position maxes out at $17 at any share price above 700; the second position maxes out at $39 at any strike above 750. The second position breaks even or makes money at 717 and above; the first position is break even or better at 683 and above (assuming full resolution next week - ignores rolling / managing the short call week to week).
Upon further review I like realizing the $15 gain I have in hand and opening a new position for next week with the $17 theoretical max gain (700 strike short call). Time to enter some trades
EDIT: or not - share price going down (and extrinsic value going up) - I'll keep waiting until closer to end of day
2nd EDIT: One downside I'm seeing with buy-writes, that I find very acceptable over these short DTE, is that it looks like they will be held close to expiration. Much like spreads - when the short option is close to the money (and at my aggression level they will be), then the time value doesn't really decay until close to the end. This is valuable to me as it makes it easier to fire and forget until late in the week, but bad for turning over positions for good gains more frequently.