My current big position is a March 19 790/615 strangle. Both legs are ITM right now, and they are quite a fair bit ITM.
And that has gotten me thinking about art of the possible and how I might handle this in the coming weeks.
The put leg is actually the easiest for me despite being ~$100 ITM. With both legs ITM, I'll be rolling the put for whatever net credit and strike improvement is available but not worrying about it beyond that. The primary risk that I see in this approach is a combination of opportunity cost and being careful about too much cash being tied to those puts.
This is also the account that is current our source for monthly income, so having unencumbered cash (or margin) is important - house, car, food, shelter - these things don't stop. Oh - and taxes. We're about to be sending in our biggest tax bill by far in another month. This is the too much cash component.
The opportunity cost arises from the shares trading down. If they were to continue trading down to $500 and then $400, etc.., then this $790 strike put won't be traipsing along, and I won't be able to take assignment at $500 for some cheap incremental shares (which I would very much like to do). More shares would be really nice, but is fairly far down my list of priorities.
This leg is easy for me as the worst case - I keep rolling along (maybe shifting to monthly rolls from 2 week rolls) until the share price comes back. My investment thesis says this is inevitable.
This is also a small change from my plan a week or so ago - I was getting ready to take a net debit to roll this for a lot more strikes for the opportunity cost reason - were the shares to keep going down, I'd like to be able to buy more (take delivery on some puts) to benefit from that. With the move back up, those net debits have been mentally reassigned to the call leg though
The call leg has become a "problem" though, despite being a serious cash generator for 6+ weeks. Many of my 2 week trading windows have seen 2 highly profitable call legs get opened and closed. But now I'm reasonably far ITM so I don't expect much in the way of net credits from the next roll and maybe for a few rolls.
The overall plan for the next roll is to tighten up the strangle and probably take a net debit on the call leg to move it much closer to the share price.
The call leg is where I am the most sensitive to being far ITM. The basic problem is that whatever strike the put leg is at, I consider it inevitable that the shares will and go above that strike. Even if it takes a couple of years, besides the opportunity cost, I've got no problems with that and my view on TSLA and Tesla is such that I have no emotional worry about how its going to play out.
But the call leg - if I "lose contact" with the share price, then there is no theoretical limit to how far behind the share price I can get. And in my investment thesis, far and fast moves to the upside are to be expected and have been personally experience by me two times ($6 to $36 post-split in 6 months; and the more recent move from $80 to $800 depending on how broad you want to make that window). I consider $5000/share by 2030 to be, if anything, conservative. Even with fewer total shares, I still want to benefit in a big way from that $5000 share price. To do so, I need to keep the call leg at least reasonably close ITM. Up to and including using the net credits from the put leg to 'help out' the call leg. OR even reaching back to previous profits and spending some of those to help out the call leg.
So though I didn't do anything today, when I start thinking about a roll on the call leg next week, I will be strongly considering a net debit roll. I don't like being most of $100 ITM as I am right now as another $100 move will still be short of where we've been recently, and would put me even deeper ITM and start being at risk of losing contact.
And the last observation I have, tying back to something
@st_lopes commented on, these deep ITM positions that can appear are why I don't like far OTM / small premium options; particularly on the call side. I've gone W A Y far OTM on some calls, and still had them go deep ITM in a short time frame. Higher premium calls provide some flexibility in dealing with these (while also increasing the likelihood that they happen).