With regard to Schopenhauer, once you say "already happened" you're already inside time. Outside of time, there is no "happened." Everything is. As for the act of freedom, no, there again you're still inside the world of representation. The act of the will that expresses itself through individual character is timeless. The part of you that experiences life is also timeless -- spend some time in meditation someday being aware of being aware, noticing the part of you that notices; you'll find that it is timeless, spaceless, and without qualities.

1) I'd consider all these 8th house questions.

2) Yes.