He also has a loving wife and two kids. He loves his job (most days) and seems genuinely fulfilled in life.

He is the poster child for that exact reason. He keeps getting the shit end of the stick... but he keeps going because he has an awesome support system that makes everything better.

It is an eternal meme. A trope. The Bibble has Job. Star Trek has Miles. Job lost his family and children to gamblor and miles loses them to the pah wraiths and a time hole. The parallelograms are there, it's in revelations people.

because it kinda implies that the moment things start looking up, a simulated lifetime of prison trauma is waiting around the next corner...

That feels about right.

Despite everything that has happened, O'Brien has worked through it with counseling and the support of his family and friends. Something to aspire to if you get your fair share of hardships too.