The first is a first person vernacular fantasy where the world shifts around from the (uneducated) narrator's perspective. All is fine and dandy until the ending. Things get deliberately confusing in the second-to-last section, and at the end things shift a lot, but there's a very specific reason for it, and a specific event that happens. Since the narrator is not clear on why this is, he can't explain, but there are clues in the last section dialogue, the way specific words are emphasized and how they refer to an earlier event. The thing is, although 5 different people have read it and all have liked it, I've gotten 5 completely different answers to, "What do you think happens at the end?" I like some ambiguity here, but nobody seems to have gotten the key event.

The other one is a pantheistic spoof, where the primary conceit is shown in a slow reveal in the opening conversation. (I know, 13 lines, but it was my first rough.) Everyone except one person has gotten the joke, but that one person was extremely vocal about how she felt insulted because she didn't get the joke. Normally I'd ignore the one person out of eight that didn't get the joke, but I'm very conscious about the line in reveals between the reader saying, "Ah, I get it, now I feel smart," and, "This writer is a jerk." I've since rewritten the opening to make it more obvious, but now I wonder if I've spoiled it for the people who like to figure things out.

Of course, the key to that is mentioning it subtly enough that the reader doesn't feel like you're shouting "HEY, THIS IS WHAT'S HAPPENING!"

If it's a character twist, where you have someone who's viewed one way and then at the end you suddenly see their true nature, it helps to try to work in hints of that nature even while you're pushing the other view. In my current WiP one of my characters seems like a truly supporting friend who's constantly pushing a PoV character to excel, and although you have hints that he's kind of a jerk you don't see until the very end just how terrible his actions and motivations have been all along.

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How do you judge when you're showing enough for the reader to get the clear picture, as opposed to shoveling it in their faces until they think they're reading a coloring book?

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This is a good question...I just finished reading a book where I thought the author went a little too far at explaining everything. I'm one of those obtuse readers who takes most things at face value, but even I had to say "OK, there is absolutely no reason for the author to keep mentioning this person unless she's going to be the person he has to fight at the end."

The thing that was missing in this particular book was another purpose for that character. She kept showing up, and then leaving in a way that was supposed to be mysterious, but no other possible reason for her actions was ever even hinted at.

I know I'm not answering the intent of your question here, and yet somehow I think it's all interrelated...You can give a lot of information as long as you hide it amongst a lot of red herrings.

For an ending, it might work to have your characters be the obtuse ones. If they can carry that load and ask the right questions:

i.e. "So why the hell did you hire that assassin to kill the regents if you were hoping to save their life? Give me one good reason why I shouldn't have you strung up by your toes right now."

If 7 out of eight people got the one story, you've probably pitched it right - you are never going to have everyone read a story the same way and that seems like a pretty high success rate to me. If 0 out of 5 got the other, then you probably haven't got that one right.