I'm typically selling between 2 weeks and a month out. My strikes aren't that far out of the money, but I usually have plenty of shares "uncovered" that I can use to help me roll up and out if needed. For instance, I am short 10 $25 calls expiring this week. If those end up deep in the money on Friday, I could probably roll out 2 weeks, roll the strike up substantially, and collect a strong credit if I BTC those 10 contracts and STO 20.