Would it depend on the amount of time left to expiration? If I have one that expires Dec 22, what would be a good put setpoint to sell to close? Don't want to be greedy, you know?

I don't have enough information to give you advice on that question.. it just depends..... I only do call options, and they are long term....

The classical dilemma in Behavioral Finance. It is all dependent upon yourself and no matter what you have to make that call and live with the outcome. I am appreciative with modest returns and try to not get greedy because there are times when I experienced pretty decent gains only to see them wiped away going "could have""should have" etc. Just pretend it's your time or a job and how much your time is worth and evaluate it that way.