I've been thinking more about these split, flip, and split-flip rolls that
@bxr140 has been talking about. And I think that somewhere in here is a cure for these 760 puts I have that are so deep ITM. I am planning to write about my journey through these things.
First a bit of terminology, as I understand and am using it.
A flip roll is a put to call, or call to put roll. I've done one of these when I flipped a -760p to a -400c last week. To pull this off one needs the backing for the new contract. In my example I needed shares instead of cash, which I accomplished by simultaneously doing an OTM call to put flip.
A split roll is a 1 to many contracts roll, but still the same kind. I.e.. 1 put to 4 puts (example). This will need a bunch of cash to support (1x76k to 4x65k or something like that).
And a split-flip combines the 2. I am today evaluating a -760p to a short call flip while adding some calls to see what is possible.
Today I'm evaluating choices on a split flip and just documenting what is available today, thought not necessarily planning to implement anything. Flipping puts to calls is better for me as I would rather turn shares into cash anyway (should I receive early assignment) and I think the overall bias is down on the shares thus calls are better than puts for finishing OTM.
A flip today takes me from 760p to 400c for a $5 credit. The 410 is too big of a stretch to still get a credit. I'm also adding a week on this from 5/28 to 6/4 (and this deep ITM I'll be rolling by Friday of this week anyway).
If I split flip to a second call then I can go 760p to 2x490c for a $14 net credit (the 500c turns into a net debit).
The split flip to a third call gets me 760p to 3x530c with a $5 net credit ($500).
The split flip to a 4th call gets me 760p to 4x550c with a $5 net credit.
The split flip to a 6th call gets me 760p to 6x575c with a $3 net credit.
The split flip to a 8th call is good for 760p to 8x590c with a $3 net credit.
The split flip to 10 calls is good for 760p to 10x600c with a $3 net credit.
The split flip to 12 calls is good for 760p to 12x605c with a $12 net credit
A couple of observations. If I'm willing to flip into enough calls then I can actually take this very deep ITM put and turn it into OTM calls. These have a 6/4 expiration, or 2 and a half weeks (1 extra week on the 5/28 put expiration that I'll roll by 5/21 anyway). I might need to look at a split flip that brings the expiration closer - like say this week. H'mm....
The second observation is that this is going to be really capital intensive. Capital intensive is a feature, not a bug, for me. But it's not all roses.
To pull this off I'd need to close all of my current covered calls in order to free up coverage for this split flip. I am in the process of doing that for expiration this Friday (-600c).
AND I'll need 600 uncovered shares to split-flip into the 6 calls for 1 put position - hence closing my current covered calls to free up shares to support this maneuver. On the plus side though I'll be freeing up cash covering a 760p to sell puts against. The obvious and certain consequence is that the income I am currently generating from the calls will stop while I'm doing this.
I'm also pretty sure, but not yet certain, that I only have the custom trade ticket that I need to make this trade in my brokerage account; not in my IRAs. I might be able to make this trade in two tickets in the IRAs. That is probably just fine, but I haven't evaluated that.
And for my context, I've already generated 2/3rds of the paycheck replacement income that is my target for the year, in the first 4 months of the year. A few months off to make all of my positions OTM is just ok with me (good even) for risk management purposes.
And the biggest part of the risk here - the shares take off on me. This would have been good for the 760p that I left behind but will be really bad for the many calls I'll be rolling into. Really bad as the move against me will be magnified by the number of calls I flip into.
Out of all of these positions, the particularly high count call positions appeal to me the most, especially if I can get similar results by rolling into weekly expirations. If I can go week to week doing something like this, then I might even be able to "cure" all of these deep ITM puts pretty quickly and get out of this perma-roll that is waiting for a big move up. A big move up that I am increasingly of the belief that we won't see this year.
More to come on this saga. And hopefully a useful view into a way to handle short options that go deeply ITM when you are willing, but prefer not, to take assignment. Kudos to bxr for the ideas!