Quote from m4a1:
which month and strike would you typically use so that there is sufficient wiggle room for the option to expire worthless?
No more than 3 months out. Typically the last 4 weeks give you the best time decay, but the farther out you go, the higher you can make the strike and still get decent premium. In addition, by holding longer times, you will have fewer commissions. (Very important). I always start scaling in since I don't know where the top exactly is. However, I do know that the top is not where the MACD is below the zero line and the RSI is beginning to diverge. I get out of calls there if I haven't already. Not an exact science--doesn't need to be.
Note: I forgot to mention in this discussion that if you sell premium that is 8 weeks or less, it is fine to bring that strke price a lot farther in. I didn't want it to sound like you would never sell anything less than 3 months out.