Whatever the stock market does, I sell options secured by my stock, and when those expire or are cheap enough to buy back, I sell more, and almost never cash in the stock. It’s slow but sure for a small-time investor.
I wish I knew how to do what you are describing. I assume you’re selling puts but how do you know which one what expiration date to choose?
The only way to make money in the market over any meaningful time is to use the gordon grown formula with dividends.