Holding 18 deep ITM LEAPS on a large cap tech name that had >100% run-up this year now at \~$500k unrealized gain, expiring June 2027. Depending on interpretation of IRS straddle rules, it becomes a long term gain in July 2026 or Jan 2027.
My goal: Let theta and IV start working for me while I wait to exit in 2027 for tax purposes, by writing OTM calls against my leaps.
How: I’d like to run a PMCC selling short calls at a strike representing a reasonably likely Jan 2027 price for roughly 30% of the current position value in premium. Thesis is collect premium now, exit the whole position in 2027 at that strike, profit off vol in the interim, and retain some upside potential until short-leg strike.
Three questions for anyone who has been here:
First, has anyone actually dealt with IRS straddle rules (§1092) on a PMCC where the long leg is a LEAPS rather than stock? Specifically whether the short call suspends the holding period on the long leg or triggers offsetting position treatment. I have a tax attorney willing to write a letter of understanding for $7-10k confirming the PMCC qualifies as a Qualified Covered Call exception. Worth it or fool’s errand?
Second (harder) question, does this structure invite audit attention in practice or is §1092 one of those rules that exists on paper but rarely gets enforced at the individual level?
Lastly, any other strategies that accomplish this goal?