A lot of what you wrote above seems to be a symptom of poor teaching, which goes to the importance of finding the right teacher. And we come around to Retro's point that when people parade around pretending to proclaim the words of the Buddha, it only muddles the issue. We should always be clear when discussing sources. Visudhimegga is not the words of the Buddha. Zen Koans are not the words of the Buddha. Those writings may have value, but we have to be clear about who wrote them and who did not.
I have only had the opportunity to meet face to face with a few wise souls, but when I did they are able to read into my question deeper than I realized I was asking, and they usually give very direct and powerful advice that acknowledges the insights I have had, while pointing to those I still need to illuminate. Most importantly, they give me optimism about my path, and a way to move forward. I don't think that's pandering, I think it's help.
I do see a dark night aspect of the path, but I don't blame it on the path. In my teens I was totally lost and miserable, so I built up this sense of self based on what society considers a good person. Now, I am in the middle of another crisis because, through Buddhism and meditation, I have seen what a sham that all was. Now I am trying to figure out how to live my life in accordance with the dhamma, which is very frustrating at this point for me. However, this is not because of the Buddha's path. It is because my past karma led me to build a life based on lies, avoiding confrontation, indulgence in pleasures, and careless waste of precious resources. Trying to correct those errors is causing me a great deal of stress, but it's not the Buddha's fault. It's not meditation's fault. It is my fault for building up a self that was bound to crash at one point or another anyway. And the way out of this dark night seems to be clearly more Buddhism, not less. When I experiment with going back to my old ways, that is when the dark night gets darker. When I experiment with going deeper into meditation, that is when the dark night lightens a bit.
A lot of the victim's of meditation you mention, I think we have to a) direct them to competent teachers, and b) realize they may have been even worse off without the meditation. I'm 90% certain I would be dead right now without Buddhism entering my life. I'll take a dark night over suicide.
Finally - thanks for your open discussion.
Sotthī hontu nirantaraṃ - May you forever be well.