Thanks everyone for their support and suggestions. I will be cogitating over all this today and tomorrow, along with taxes.
But first, a nice nature hike to feed my spirit.
I certainly understand the concept of rolling the ITM CCs out, even to 2025, to gain time, increase strike and save them from early assignment. However, that is probably not a good financial strategy: selling LEAPS for a company growing earnings exponentially at half the ATH. I didn’t want to sell at 400 in 2021, so why is a 300 strike 2025 better? Let’s just admit the lunacy and close them (or get them OTM for the week as quickly as possible).
Unfortunately,
@Oil4AsphaultOnly I’m not sure how to flip an ITM CC into a CSP in my non-margin IRA account. The CSPs require cash backing and buying back the CCs requires cash, of which I don’t have enough.
In one account, all shares are CC’d and there are no CSPs (or much cash) left. I’ve committed most of the remaining cash into a small number of BPS spreads (allowed in this IRA). Since the BPSs are diametrically opposed to the CCs, one or the other must lose value. The CCs have such a large negative value that my overall account balance will actually improve if the BPSs are challenged. There
are CSPs in the other account, but in a 1:2 ratio to the CCs. Enough cash to buyback and close the CCs, but not much will be left after those transactions. As with what
@BornToFly has done in the past, I will probably “do half”: buyback 1/2, roll 1/2 to OTM, and sell OTM puts or ICs with any remaining cash.
Ultimately, if the SP continues on the current trend to $300, it would be best to close all CCs as early as possible. Unless the rise is less than $5/week (2-3%), selling even OTM CCs makes for very little premium and lots of risk. In an uptrend it’s better to sell BPS or buy ATM CCs. There is very little theta decay at $50 ITM, and there certainly won’t be any at $100-$150 ITM. Unfortunately, the best I can hope for is a small SP pullback and oscillation around $200+/-$10.