1. You are missing the key strategies to mitigate risk: covered call and covered put. Writers/sellers of options use these strats to protect them from taking a huge loss if the stock moves sharply against them. Just selling a call/put without covering/protecting is called naked, and it can be quite risky. [A, B, C] Note that a covered put and a protective put are two different strats. [D] 2. The further out of the money you go, the lower premium you'll pay. 3. If the stock moves sharply, or moves out of hours, you will not be able to sell shares. The price will move directly up or down, and you will not be able to gradually sell as the price moves. As a retail trader, if you submit a market order for a rapidly changing instrument, you're last in line; you'll get the worst price, and stuck with a big loss. 4. I like Interactive Brokers, but more for the API than the charting. A. The Basics of Covered Calls (investopedia.com) B. What Is a Covered Put? | The Motley Fool C. Naked Put Definition (investopedia.com) D. Protective Put Definition (investopedia.com)
Covered calls don’t mitigate risk. When a stock falls 30percent, the two percent you received selling the call will provide little comfort.
your current broker. get TDA's thinkorswim client, the "risk profile" graphs are what you're looking for