To profit from rolling, mustn't you be much more bullish or bearish than before?
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.