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by opportune 1972 days ago
What I mean is that wheeling on SPY is less lucrative than even buying and holding SPY over time, because they are lower risk; see the linked post with backtesting. The past year is not a great example because we have had periods of higher-than-normal volatility.

Of course, you might have better luck wheeling on something with much more implied risk than SPY or cycling through some of the most risky stocks. But depending on where you are in the wheel, you are still yourself assuming risk that can make you lose money (e.g. a collapse in implied risk while you hold the stock).

When you say wheeling works best on a stock with low volatility and high OI, what you mean is that it works best on a security with under-priced risk. I am sure there are actually many funds running strategies based on exploiting over-priced risk premiums. They just have no need to trade options on the open market since they can work with a market maker who can take the other side for them.