I skimmed this thread, but I don’t think Robert has said anything foolish.
There’s nothing wrong with selling cash secured puts unlevered. He’s taking a view that the premium received will compensate him over the long run.
I don’t see anything wrong with his strategy of rolling his puts down and out to preserve his premium. he hasn’t increased his risk. He’s not doubling down as much as he’s extending his duration.
His strategy should perform with about (maybe slightly better) the same sharpe as the overall market. I certainly wouldn’t qualify it as picking up pennies in front of a steam roller as he isn’t any more leveraged than a buy and hold investor.
I am now a believer that with knowledge and judgement (don't over leverage), one can make a good living going long, going short, trading single leg or in any combinations.
My dear friend has been writing calls and puts for a living for over 15 years. He wrote calls/puts on the same stock all these years. It wasn't done mechanically.