I was wondering how all these experiences are comparable. 

In Dan Browns book on Attachment Disorders he names a range of meta cognitive skills, from beginner to intermediate to advanced. From what I know he views awakening as a meta cognitive skill that needs to be developed over time. In his book the advanced states of meta cognition refer to advanced meditative skills. 
Stanislaf Grov coined the term "Condensed Experiences" (Coex systems). Following his description of these events, humans can randomly stumble up on them and awaken spiritual energies that mostly result in personal crisis. Here the notion seems that several layers of trauma (pre natal, past life etc.) are all interacting. The goal is not healing as in recovering but becoming "whole." 
In his work he describes that his clients would first work through personal layers and later on would enter the collective unconscious.
These description are also very based on Jung's work. In Buddhism they would refer this to the Heart Sutra. 
Since I don't believe that Grof's patients & people who came across this were all hardcore meditators with an abundant range of meta cognitive skills, how would such a person be categorized? Dan Brown saw secure attachment as a preliminary for meditation practice. Securely attached adults have significantly higher coherence of mind, which in other words is better meta cognition. Unfortunately approximately only 50% of adults living in the west have Secure Attachment. How are these experiences then categorized? Is someone with an awakened heart enlightened although he/she possesses terrible meta cognitive skills? 
From my understanding of the Heart Sutra, the Theravada paths are inferior to the awakening of the Heart.  
This is obviously just a limited attempt of the mind to make sesne of these things. Please forgive the grammar and typos. 

I don't think I fully understand your question but for what it's worth, trauma can mimic early stages of insight by dissassociation. The disassociation caused by the intense experience creates a sense of "witnessing the body/mind as not self". For example during a car accident we can experience such pain that part of the mind seems to separate and witness it and the body is seen as not being the same thing as "me". 

So trauma can create condensed experiences of witnessing which is similar to early stages of meditation insights into "not self".

Just one note: the term metacognition has a wide array of completely different meanings. E.g. Culadasa's metacognitive awareness, metacognitive beliefs from MTC, Brown's metacognition... I don't think anybody has a full picture of how all these mental faculties are related to one another and to meditation.

I should have been a bit more specific. I was wondering if people who stumble across awakening spontaneously or in therapy can have the same insights as Vipassana practitioners.
In the internet forums awakenings/paths are highly regarded. In Stanislav Grofs work it seems as if they are a natural occurrence that can happen to anyone anytime without spiritual practice. Are these insights then comparable, or are they regarded as experiences, whereas the insight paths are much more difficult to obtain? 

That's sort of an abstract question. I'm not sure something that general could be answered in a real way.

Kiran Trace's story directly addresses your question I think. They specifically discuss it on her BATGAP interview. 

  Also, keep in mind that much of Stan Grof's work is based on his therapy sessions with patients on LSD which he did a lot of before these new compounds became illegal. Hoffman who synthesized it in switzerland sent samples to scientific/clinician colleagues throughout europe, and Grof was one of them. I think that's why the descriptions are so very dramatic.

I do think, though, that lots of people get emergent experiences spontaneously, or at least without intentional cultivation, but then the higher levels of development usually take dedicated practice. 

If you look at Grofs' typologies of spiritual emergence(y), for instance the division between biographical, perinatal, and then transpersonal experiences, there is indeed, as you suggested, a sort of developmental model there. For instance one could look at the book "The stormy search for the self", chapter "Modern maps of consciousness", I believe it is. And the progression is actually quite reminiscent of a sort of extremely dramatic/archetypal/vision-heavy version of the POI.

Perinatal experiences for exemple, seem like textbook dark night stuff. There are subdivisions in there, too. Grofs' theory, based on Otto Rank, is that the perinatal experiences are actually traumatic birth memories being fully experienced. That would mean DN stuff is related with the birthing experience. For instance the description of the specific type/phase of perinatal experiences that corresponds to the very moment of birth (going through the birth canal etc.) is extremely close to the "Re-observation" ñana. An interesting thought, though I really doubt that is the whole story. 

In any case, Grof does mention a broad variety of triggers and specific practices one can do to deepen these experiences and further this sepcific form of development he called spiritual emergence — including meditaiton and the likes. They even invented their own technique, called Holotropic Breathwork (TM). There are definitely merits as well as shortcomings in the Grofs' work, though. His theories about what is going on with spiritual emergence are, I think, somewhat arbitrary, sometimes far-fetched, and don't seem to have actually been tested but just gotten adopted by transpersonal people without much criticism of the metaphysics implied there... 

Anyways,  back to your question:
My 2 cts is that it's both — i.e., they are a natural occurence that can happen to anyone anytime without spiritual practice (Daniel once told me he thinks between 5-25% of people have crossed the A&P), and the higher levels of development are much more rare and difficult to obtain (SE: less than a portion of 1% of people ?).

Cheers !