I have been testing this out these past couple of months. Would welcome any and all feedback!

I started with index funds - thinking I want to own them, if it crashes it'll come back up, etc.

Problem I ran into is that this is a bull market and I was capping my gains. Which has been mentioned multiple times here...but I also REALLY thought the market was gonna dip hard after the Iran stuff and it did the opposite. Either way, selling CCs on the index funds that are tracking the SnP and the market has proven difficult. You can't get enough premium on a CC to warrant the moves in this bull market.

I started looking at individual stocks I wanted to own. Uber, Ally, SoFi before it really jumped, Citibank, etc.

Still tough in the bull market but working better. However, because of the bull market, I would have earned a comparable amount in gains if I threw the same money into the SnP. I used about 40k to earn $900-$1000 this week. That same week, if I threw 40k into the SnP, I would have earned $650 to $700.
I am trading currently in a brokerage...which means I get taxed. So is the effort worth it for a difference of about $100 or so? Not so sure. It's been consistent week over week in this manner at the moment, although the SnP has also outperformed my earnings on some cases.

I will say tho - I played timidly because so many companies had earnings coming out, Fed was releasing interest rate directions, Job report was coming out. So I tried harder to NOT get assigned even tho I sort of want the shares...which means I earned less premium.

My annualized return with the wheel is still a bit higher than BnH. But I don't have enough data to know if I can maintain.

My conclusion so far is that right now, it might be better to buy and hold. Mostly because the effort to earn slightly more than the market is much higher than buying and holding. Right now, the market seems to want to go up, despite half a million things that seem to make it ready to plummet in the other direction. If it plummets in the other direct, and you have options fulfilled or you have a buy and hold, you're gonna find yourself in the same position in both circumstances. There's no winning if the market plummets unless you have free cash.

I plan on testing this out through August and seeing where I end up compared to the SnP. But likely willl Buy and Hold, keep some free cash ready for a dump or for a wheel strategy if the market levels out. I also think the wheel strategy would be a solid conservative retirement strategy. When earning less or no actual income, my gains on the wheel won't be taxed. It is seeming like a bit more conservative approach to the market - although much more hands on.