FWIW I have an account with $30k cash that I sell 6x $50 weekly put spreads in (fairly well OTM). As it’s grown to $35k/$40k cash I’ve upped it to 7x then 8x then 9x $50 spreads (I squeaked out 9 because the premium earned basically counts as additional backing cash). If the stock price crashed and stayed low, I’d likely lose the entire sum of cash. I have other things in the account so it wouldn’t be devastating, but it would sure be a bummer. (I am not concerned that an oddity of closing prices would require more cash than I have to back the spreads; I’m diligent about closing/rolling each week.)
When the stock dropped nearly 20% in 2 days just recently, my spreads (then at $1000-1050 against a stock price of $1200+) went partly then fully ITM before I reacted… I just hadn’t thought that big a drop was plausible (oops) and it looked grim for a bit… but fortunately I was able to roll out a week for a profit when the price waffled up from time to time. Actually with the volatility the option pricing is high enough that I made just as much as usual in the rolls though they would typically go right back underwater shortly after the roll.
I was prepared to roll for little to no profit for a few weeks until the Q4 numbers or factories opening… Then yesterday it seemed like I might be out of the woods. (We’ll see if this holds?)
But, worth noting, if the stock price really tanked I would have few choices. Once deep enough in the money the roll options might have been for a debit (and I don’t want to throw good money after bad) or at in increased strike (not that attractive if stock is tanking) or farther out in time (though small spreads don’t do as well moving out in time) or widening the spread (requiring more cash backing; see good money after bad). If I had started this in what was it, February or April it might not have gone well?
So, I wouldn’t do this with money I can’t lose, or with a stock I don’t have confidence in… my goal with this scenario is to keep selling more spreads as the backing increases until I get to the point that the spreads throw off about $5k each week and then I will keep the spread count steady and invest that cash… hoping that if there is a total loss in the future, I will have at least generated enough income by then to feel like I can accept the total loss, sell $30k worth of shares, and start over.
Maybe if you’re going to try paper trading it would be good to have some kind of goal like that in mind, rather than just sort of ad hoc trading.