Nate, I know all about the questions you're asking yourself because I ask myself those same questions every night regarding Winston. I obviously know that there's a big size difference, age difference, etc. between the two, but we're still working on trust when it comes to handling Winston. Basically, he doesn't want to be held or touched at all - by anyone, even Jerry (outside of beak to beak contact - no preening or anything of the sort though). Yet I can walk up to him and literally have my face an inch or two from his, and we can talk and play the blinking game. As soon as those hands come too close to him, no matter how slowly I move, he gets scared and flies away. And just last night I was telling my husband, who always questions why it's taking him so long to step up, that we know NOTHING about his past. For all we know his first home may have had a child who would walk past his cage and smack the cage or poke their fingers at him through cage bars. He's not a baby and we just don't know where he's coming from.
But he DOES trust us - trusts us to be in his cage and near him in general, just as long as we don't try to touch him. And he does want to be near us. And he eagerly steps up on a plate/bowl of warm veggies that I'm holding in my hand.
And last night was just the tiniest little improvement ever, but Dave and I both noticed it. Every night we do offer our hand and ask him to step up, and he promptly flies away. Last night, Dave offered his hand and - he thought about it.

He cocked his head to the side, looked at Dave's hand, and didn't fly away. We could see the wheels turning. Some might not think it's progress, but we both recognized it.
Also yesterday Jerry and I were really playing together, he was all wound up and we played together for awhile and every so often I would peek at Winston out of the corner of my eye and he was watching us the whole time, and at times even quivering his wings - I believe out of wanting to come over and play (we were having fun and whooping it up) but being nervous since I was so hands-on with Jerry.
So yeah, I know the feeling of not wanting to push but at the same time try and make some headway - it will come.