thisiscurio
I used to create blogs with hopes of gaining 'financial independence' because I idolise those many and reproducing gurus gallivanting around the net space, those who told me it is possible despite the disclaimer "only if you work under an unspecificied amount of hard work". But I'm tired of trying again and it is probably my fault that things didn't pan put well. Right now, I try to write like I used to; I write because I love writing even if my skills are abysmal at best.
Though, aswering your question, it's indeed getting more difficult but escalating difficulty is all that happens when the rack and pinion of progress and keeps moving.
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.
My usage of "care" here is equal to "notice". To make it easier for myself, I imagine an anthropomorphic universe gallivanting around and notice one of its agents doing something that could possibly exert an effect (either null and non-null) and bless it with that effect after spinning the wheel of probability.
The universe doesn't care who you are the same way a benevolent god cares about his subject; the universe cares about you in an impersonal kind of way, that is if you do things according to the reality that is already established, then it'll 'care' about you and give what you want. The giving is likely probabilistic.