I’ve been selling cash-secured puts and covered calls (the "Wheel" strategy) for a while, but I’m struggling with the data side of it.

Most brokerages (IBKR, Schwab, Robinhood) treat every contract as a siloed trade. They don’t automatically "decay" the cost basis of my underlying stock or LEAPS when I collect premium. After rolling a position three or four times, it becomes nearly impossible to see my actual break-even or true annualized ROI without a massive, manual spreadsheet.

I got so frustrated that I started building a tool to automate this for myself: PremiumFlow (https://premiumflow.base44.app/).

My approach was to create a dashboard that:

Automatically adjusts the cost basis of a position as premiums are collected.

Tracks "Poor Man’s Covered Calls" (selling against LEAPS) properly.

Monitors assignment risk for ITM puts in real-time.

I'm curious how others in the HN community handle this:

Do you have a "holy grail" spreadsheet that actually works?

Have you found a third-party tool that handles the "cost basis" problem correctly?

Or do you just rely on your brokerage's (often confusing) tax lots?

I'd love to hear about your workflow or any feedback on the tool I've started building.