I suspect that awakening is really hard and dangerous when life is really hard and dangerous. But beyond that trite tautology

here's what I see as the danger points:
When enthusiasm for practice becomes indulgent and can become mania,
When concentration starts getting strong and begins to turn back inward and objectifies emotions and thoughts and can create depersonalization.
When the non-tangibility of thoughts and emotions start becoming obvious (dark night) and can create depression/nihilism.
When the "manipulation" aspect of applying a method becomes evident, which can create a profound sense of disillusionment with practice... and ending practice too soon.
When the motivating fantasies of enlightenment itself start falling away, which can lead to a profound sense of anger and despair... and more depression.
None of these will really make you go mad, but they can be pretty tough. Having a teacher (like I had with Hokai) and senior peers (like you were for me Chris) really does help. I think I recounted the story that when Hokai was helping through the last bit of work he basically said, "I'm sorry but this last part can really suck, basically you're going to see that everything you thought this practice was going to give you is just a need you have due to your own woundedness" (those are my words, not quite how Hokai would say it). Anyway, that sort of heads-up can probably make the different between going bat-shit crazy and just enduring the discomfort of dealing with some difficult stuff.
p.s. I chucked at his statement about people being "garbage bags of negative entropy"... mostly because a while ago I was trying to capture the common theme of what I spend most of my time thinking about and it was: the philosophical ramifications of the entropy of this universe.