I was going through a script full of flashbacks the other day. The flashbacks seemed unmotivated to me. The scenes themselves were important to the story, but I didn't know why we were flashing back at that point.
I think the best rule is: Use a flashback when the audience has just asked the question that the flashback answers. Which means, of course, that you provoke the audience to ask the question, and then you provide the flashback that answers it.
This is actually a pretty good rule for any sort of cutting away from what the hero is doing right now, whether it's to the past or the future or to another character. When I'm telling a well-crafted screen story to my stepson, I find that he often asks a question just before I come to the part that answers that question. That's good story telling. Let the audience ask the question, and then answer it for them. When the audience asks the question, they pull themselves into the story.
By contrast, just pushing information at the audience tends to push the audience out of the story.
You can, especially in TV, cut to the B-story just to trim the A story -- it's always easier to jump from one time to another time when you jump to another story in the middle. But if you can relate the B story to what's happening in the A story, that's usually stronger.
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