Hey, thanks for all the responses

To clarify, in my original post I didn't mention anything about the 4 being more difficult or tortured or special or anything, I said more painful. I notice that much of my daily life is painful, and that development often comes with growing pains. I notice that pleasure in meditation is very rare for me... like the ratio is probably something like about 1 hour of pleasure for every 20 hours of pain, roughly speaking. The idea of a "bliss junkie" seems so foreign to me. I have seen people who look like they may be bliss junkies, but I have never understood how they got there. It seems that first you have to have the capacity for feeling bliss before you can become a junkie with it.
(Maybe I am just not very skilled at meditation or something?)
Oliver Myth:
As far as four being the most painful, I think its more about the way they think of their suffering. I notice that fours try to be perfect socially or internally or whatever, and when they fail they assess themselves over and over. Thru that re-assessing they tend to identify with not being the person they want to be, so their suffering comes more in the form of self-blame...
I think this may be part of it, but I wonder if it might be something more fundamental, like the way in which the body physically contracts in response to stimuli, or perhaps the way in which sensory information is processed in the brain. My experience is that even if I take all the story out of it and the assesments, it seems that this sense of self is regularly contracting into painful tension patterns, and in someway it's the contracting which is somehow reinforcing the sense of self... like the ennea-4 gaining a sense of identity through this pain.
Oliver Myth:
I found AH Almaas's book to be the most rich and yet confusing book. Its meant for folk past 4th path MCTB as far as I understand it.
Yes, I read much of that book and enjoyed it at the time. I don't think I was personally past 4th path but still much of it made sense to me. It is a very different take on the topic. I haven't read any spiritual books in a long time, however.
Fitter Stoke:
Yet in practice, all I ever see is people using enneagram to deepen their identification and to script themselves into worse neuroticism...
Yes, this is why it took me two years between the time I first read that book and when I posted here. For the most part, I think the enneagram can be fuel for neurotic psychologizing.
However, I think there may also be something physical to it, like genetic perhaps, and that it may be more than just a "story." It's like if I had some physical disease I would want to diagnose it and treat it accordingly, not just say "drop the story." I'm not necessarily saying that ego fixation is a disease, but it has some similarities.

Andrew Ken:
I am also quite clearly a type 4. Reading the descriptions about what a type 4 is makes me cringe. Sounds like the worst type to me, haha.
Yeah, I feel for you.

Andrew Ken:
I'm not sure how it could even be possible to measure the actual suffering that different types go through.
It's tough to measure a subjective experience, but I think there may be quantifiable variables at play.
I actually don't think there would be any correlation between suffering and enneagram type, because everyone suffers. So, perhaps I should just stick to the term "pain." Pleasure can also be full of suffering, but I don't think I experience this type of suffering as often.
Andrew Ken:
insight practices are about getting a clear/er grip on the absolute self and the enneagram stuff on the relative self, and getting them mixed up sounds to me like the type of thing Daniel Ingram cautions us against in MCTB, imho.
what do you think?
I absolutely agree that they are different practices. I think the type of sensations that are experienced in this moment are absolutely independent to the realization that those sensations are impermanent, unsatisfactory, and not-self.