Quote from Cache Landing:
It isn't about static analysis. When you sell OTM and the underlying moves against you, then you must buy back the position at a loss. You then sell a larger quantity further OTM with the same expiry. The premium recieved from this new position was determined not by the previous static valuation, but by the current probability that the short strike will be breached again by expiration.
In this strategy you are simply accepting the loss from the first position along with greater risk on the second position, that will allow for a profit big enough to offset the original loss. After every adjustment the R/R is less favorable. In this sense the strategy banks on the idea that your bank roll never runs out. I admitted that this strategy prevents short term loss, but anyone who recommends this to a small account novice is irresponsible at best. The initial position would have to be so small that commissions would completely wipe out any potential profits.
Unfortunately your initial post had static analysis all over it when describing how all the small gains would or could be wiped out by one move because of the odds game. That assumes same position size. Also, my recommendation to novices is deep out of the money and is the most responsible strategy for a novice. You must shop for low commissions.