I have studied GR in some detail, so I am aware of all these possible scenarios; by personality I also tend to be a “natural worrier” who easily gets anxious even over minor things and life events. In addition, I am an Aspie too. Yet I feel no sense of depression, worry or anxiety over the possibility of a cyclical cosmology. Furthermore, you need to remember that the observational evidence we have at the moment is much more consistent with other global topologies, and not a cyclical universe.
I believe you when you say that you yourself might find such an idea depressing, but remember that this does not imply that others necessarily relate to the concept in the same way. Most of us here understand the notion of a cyclical cosmology well enough, but don’t find it depressing.
I find that people often tend to miss the salient point of Schopenhauer’s philosophy - he did not advocate despair, depression, or absolute nihilism. The main point he was trying to make was about acceptance. It is strictly necessary to fully understand and acknowledge the inherent limitations of the human condition - such as the impossibility to permanently satisfy desires and craving, and the futility of constant strife towards some ideal utopia -, but then it is also necessary to accept them for what they are, and thus arrive at a position of peaceful coexistence with those limitations. Philosophical pessimism does not imply despair and meaninglessness.
And of course, philosophical pessimism is only one possible life philosophy, which is by no means shared by everyone.