I really think you need to put these quotes in their proper context, as I've pointed out before: CTR taught the Vajrayana and Maha Ati within the scope of the entire path, he outlined all 9 yanas in great detail: he was careful to contextualize everything so the Dharma was completely taught and transplanted here- not just part of it.
Alpha-purity -- Trungpa Rinpoche's translation of kadag -- is
always prior to any notions of "Buddhism." This is why atiyoga is a complete yāna in and of itself. And alpha-purity cannot be institutionalized, domesticated, boxed and packaged. The earliest phase of atiyoga tantras -- which have been referred to as "pristine dzogchen" or "radical dzogchen" -- are far more critical and dismissive of all features of every temporal yāna than is often acknowledged. The same is true for the Indian mahāsiddha dohas. That atiyoga and mahāmudrā are at times boxed and packaged within the constraints of sequential stage practices of conceptual yānas shouldn't lull one into a false sense of security by conceptually attempting to distance the sheer immediacy of this radical view. Keith Dowman's introduction to Old Man Basking in the Sun
Although all such religious practices [of the eight yānas other than atiyoga] are distinguished by varying degrees of subtlety and sophistication, they are all goal-oriented, and as such a conceptual distinction is implicit between what is and what should be, between samsara and nirvana, sentient beings and buddha. Striving to attain a spiritual objective is implied in all these approaches and it is here that Dzogchen defines itself outside the frame of religion and tantra-yoga. Dzogchen stresses the undeniable fact that any goal-oriented conscientious endeavor assumes a result in a future that by definition never comes and thereby precludes attainment in the present moment. Thus there can be no liberation until the drive to attainment is relinquished. In this important sense, every path of religious striving is a dead end and represents a deviation from the natural gnosis of pure mind, 'the heart of the matter'....
It is therefore an error to assume that one is 'not ready' for Dzogchen because of a lack of study and intellectual preparation. Initiatory experience is present in this very moment and nothing can be done to facilitate its advent. Any kind of preparation or fore-practice muddies the waters in its assumption of a goal to be reached. Access to the clarity and the zing of reality, on the contrary, is more likely to be found in an innocent pristine mind that has not been conditioned by the cultural and religious assumptions of a 'sophisticated' tradition. Purity of karma, putative rebirth, guru-relationship, degree of meditation-concentration, facility in visualization, levels of attainment, and so on, are all issues pertinent to acceptance and success within a hierarchical cult wherein a particular ideal form of social and psychological behavior is a goal to be achieved; but to the formless experience of Dzogchen such considerations have no relevance. Striving in any kind of preparatory endeavor is an exercise in shooting oneself in the foot, or at least running after a mirage. In fact, to reach the point of relaxation in the moment that provides intimation of gnosis, non-action is the sole precept.
This perspective in radical Dzogchen is exclusive to those who have no need or inclination to exchange their inbred cultural norms and mores for those belonging to a more exotic or 'spiritual' tradition, or to reject their cultural legacy and educational conditioning in an effort to change their psychological make-up. Recognition of our lived experience, just as it is, in its miraculous immediacy and beauty, without any yen for change, is the praxis of radical Dzogchen, and belief in personal development and improvement, progress towards a social ideal, moral evolution of the species, and so on, is deviation from the pure pleasure of the unthought timeless moment.
Is this expression radical? Yes. Is it potentially dangerous? It certainly is. And this is precisely why it is commonly considered skillful within the institutionalized traditions to present this view to students after some degree of ethical conduct and conventional altruism have been instilled. Nevertheless, the radical immediacy of self-occurring gnosis (rangjung yeshe) cannot be meted out piecemeal.
Further, Ray has taught the Śrāvakayāna and Mahāyāna according to the presentation style of CTR, and there is no reason to believe that he doesn't continue to do so.
Hopelessness actually functions much more effectively in the context of understanding cyclic existence, transmigration, the inevitability of karma -and the claustrophobia of knowing that the effects of all your actions will return to you-- that there is no escape from interdependence, etc. Just being agnostic about all of this creates much more space for hope to arise.
Now it seems that you're attempting to qualify hopelessness in order to blunt the cutting edge. According to CTR "hopelessness is the essence of crazy wisdom."
Robert Thurman points out in one of his talks how most people that believe there is "nothing" after death are generally finding comfort in that, in the idea of a peaceful final slumber from which they'll never have to awake.
Ray isn't promoting nihilism.
So I very much disagree with your interpretation of what Reggie is saying, and I don't think he is honoring the quotes that you left us with, at least not at the face value of what he is actually saying in these interviews. You do seem to be stretching these justifications a bit far, and I wonder what you're really getting at.
Reggie Ray and Ani Pema are likely to have a more comprehensive understanding of what CTR was pointing to than you do.
All the best,