To profit from rolling, mustn't you be much more bullish or bearish than before? Aren't you likelier to lose money from rolling, e.g. scenarios 3-5 below? How exactly can rolling profit you?

What if you aren't more bullish or bearish than before? What if you surmise that the underlying stock will attain only a certain range of prices, and de/in-crease no further?


I'll brainstorm three cases. Imagine that:

you bought a call. Your underlying asset's price hasn't risen above the spot price on purchase date.

you bought a put. Your underlying's price hasn't dropped below the spot price on purchase date.


In both cases, your call's and put's prices will have dropped, and you've lost money.

your underlying's price de/in-creases beyond the purchase spot price. Then all options' IV may rise. Then even puts at lower strike prices and calls at higher strike prices will cost more.
If markets are efficient, the option premium will equal the expected return on the option. This is independent of the past history of the underlying security.
In order for the past history to matter, you will need to demonstrate market inefficiency. It is possible to demonstrate some market inefficiencies (e.g., the fixed income pricing literature is generally premised on the existence of a term risk premium, the issue is how to estimate it). However, future returns getting a risk premium based on recent historical price movements would be equivalent to proving that technical analysis can reliably outperform (on a probabilistic basis). Finding validation of such a possibility has been a major challenge for researchers.