Position size is the biggest challenge. My position size was often too large for short futures and equity naked calls. I took much larger drawdowns than expected with silver, oil, $CAR and $AXTI. For each, the concept eventually worked. But, too large an initial position meant that the portfolio was rocked until the trade started working. I need to start smaller and have more patience in sizing up. On the other hand, for conventional covered calls and cash-secured puts, I probably sized too small initially.

Options-related yield was a much more significant driver than dividends. Received a bit over $12k in dividends, but several times that in options premia.

Interest matters. I chose to house the experiment at Interactive Brokers because it pays substantial interest on balances, including those from selling options. That move paid off even more than expected. Since its Dec 2025 start, the portfolio has earned over $7,500 in net interest (interest received - borrow fees paid + short yield enhancement program payments received). That is much more than the commissions paid during the same period.

The portfolio is difficult to track. I tried a number of off-the-shelf products to track the portfolio, like AllInvestView and Wingman Trade. None worked well. Some wouldn’t update data automatically. Most failed to properly group trades together. So, I spent several hours with Claude CoWork and Claude for Excel, and now have a viable tracker. It’s pretty amazing to be honest since I cannot program at all.

The qualified covered call rule is both important and challenging. When a covered call position appreciates significantly, you see a large gain in the underlying and a substantial loss in the short call. If a few qualifiers are met, our tax code allows you to pull off a tax trifecta: take the call loss in the current tax year, postpone the gain on the underlying, and let the underlying age so it can eventually get long-term status. But, another squirrely tax rule prevents you from just rolling the call component into a later period. That rule requires a 30-day waiting period after a loss is taken before entering into a substantially similar position. There is no way to avoid being fully exposed for a month. So, when faced with a heavily appreciated covered call, the big question is when do you pull the trigger? If you cover the call and the price drops (as happened to me covering a call on QCOM earlier this month), and you end up taking a much greater loss than needed on the call component. Or the stock could appreciate after you cover, putting you in a great position to re-enter the call after the 30-day wash sale period expires. As far as I can tell at this stage in the experiment, its largely guesswork and the results a matter of luck.