You've killed us both

[Kein]

"a man that could escape The Shadow so much times" would have have likewise been able to escape in all three endings; he didn't, so that theory doesn't work.

I failed to see how it does not work. Show me teh sane proof that he SHOULD to escape from teh Shadow in all endings. What the point of then of all those 3 the same endings, lol?

but even if it did, the problem still remains as to why it didn't 'decide' to take him in all endings

Sigh.
As I told you, Daniel gets killed in 1st ending, CAN'T be killed in 2nd coz he escaped and temporary escapes in 3rd (temporary coz, as the game states, you can't escape Shadow, it will took you eventually). Where is the contradiction that scratches your mind and steals your sleep? I see none.

Yes we rejoin with Agrippa & Weyer, but you're mistaken: this only happens quite clearly after The Shadow has taken Daniel. We see him die, he most certainly did not escape alive, and so The Shadow also takes him in this ending, yet not in all of them, leaving the contradiction.

No offense, but that's exactly why I hate fanbois. TONS of unrelated fantasies and crazy explanations without any solid facts. We didn't saw him dying. All we saw is the agrippa's head in the portal and then blackness. Period.