https://www.linkedin.com/pulse/worried-stock-market-crash-heres-how-you-can-tail-hedge-jesse-felder
I am considering employing a strategy similar to that described in the link above. Being relatively inexperienced to option trading, I have obvious concerns about not fully understanding the implications of such a strategy. I realize that many will think to offer me advice to steer clear. Thank you for the advice and I may end up heeding it. But I need more information before I can decide what works best for me.
I understand that the majority of the time I would roll options and 'lose' money. That seems like the easy part. Most of my questions center on what happens if there is a large down move and suddenly the puts are ITM:
-- Would there be any risk in a crisis that I would be unable to sell the now ITM-puts before expiration? I am trying to understand (1) what the probability is of not being able to sell the puts and (2) what would be the process if they expired in the money--would I need to come up with 5000 shares of SPY to sell at a profit? What if I don't have enough capital to purchase?
-- Let's say I bought contracts for October expiration on Sept 1, and around Sept 15, there was a large down move (30-40%) and those puts were now ATM or ITM. Would a smart investor sell those at this time (and purchase November expirations) or hold to the end of the month and roll them into a Novembercontract? Would the prices of November OTM puts likely increase significantly in the setting of such an event? Will liquidity be negatively affected in the setting of such an event?
Thanks in advance to any replies or advice.