Life Is a Cardboard Box

[Tears in Rain]

People who are suffering in this way have ample motivation to directly chase freedom, yet attempting to use awakening to escape the trauma doesn't work.

Why not? Everything goes, the good, the bad, and the ugly(including trauma). Everything gets deleted.

It isn't clear if I am destined to get anywhere on either front in this lifetime

Probably not.

Some people arrive at spirituality because their lives are a disaster, while others are at the opposite end of the spectrum: they have gained everything that is supposed to make someone happy, yet are acutely aware that something huge is still missing.

Makes sense, people look to spirituality to try and deal with their shit.

Then there's the actual state that aspirants are striving for: an awareness of being completely timeless, (no birth or death) one with everything and free of all problems. It

That's not what aspirants are striving for. It might be what they think they're striving for, but what they really want is some kind of imaginary blissful fairytale life.