Ahhh, glad you already get it ^_^ It's one of those dynamics too few people understand. (And my sympathies for any of it that was learned in a difficult way.)

This Stephen definitely had the "playing victim when you're not" tendencies drilled out of him early on, and he's spent a lot of this AU learning to guard against actual victimization.

I'm not sure I'd say he's better off overall -- the vulnerabilities you noticed do make him easier to exploit, and I don't want to sound like "ooh, canon!Stephen should've been abused for several decades, he'd have come out better off." But I think you're on to something, in that Stephen Freem has had the luck of ending up surrounded by loving and supportive people, and wasn't able to block out help when he most desperately needed it (even if that's caused new problems down the road). He has the drive and the support to make himself better-adjusted. Canon!Stephen is too attached to his toxic acquaintances and his general defensiveness to make any changes for the better.