I have really enjoyed this discussion and it saddens me that my 1st Run of DC is in storage right now. Not good.
Just going by what I remember, but I recall reading the story where they must return to the planet from "The Apple" and Kirk realizes the decisions he made in his early 30s were not perhaps the best. One of the issues ends with Spock effectively telling Kirk he must live with the choices he made all those years ago. I enjoyed it very much.