What is the best way to track when an option becomes in the money and be alerted to that?

Answer 1

The absolute best way I know about is to subscribe to a service online that offers REAL TIME options prices rather than delayed options prices. Try the services of Scottrade or other reputable online provider. And to make sure you're alerted, you can buy software that will actually ring a bell on your computer. You might possibly be able to do something similar with your cell phone.
But to really solve this problem, why not establish your goal and place a limit order GTC (good til cancelled). That way you can enjoy your free time and not even have to worry about getting your trade in. As you know, most options expire worthless anyway; however, what keeps people involved are those high potential pay-offs. We had a saying in the brokerage business about options trading: "The pigs get fat but the hogs get slaughtered." So set a realistic goal that you're happy with and don't ever worry about what you "could have" made. Feel good that you made a profit where most will experience a loss. Good luck.