Thought it might be bleak for those who are ill-equipped to deal with the modern types of chaos (eg anxiety and depression). Like someone else said, this could all be a matter of labeling the world as "good" or "bad"; the problem with these labels is that they are rarely self-examined partly because it takes a lot of epistemological thinking and self-awareness to reach that level of meta-cognition.

From your points on conflation, just to clarify, are you saying that meaning does not determine our feelings about the degree of bleakness? Maybe meaning is a multiplier of feelings depending on the direction you are interested in. For non-bleakness, meaningfulness would multiply the amount of enjoyment, and for bleakness, non-meaningfulness would multiply the amount of hatred. Those two assume that state of bleakness is naturally attached with intrinsic feelings.

I wish I've read more about this topic; it is ultra interesting.