Dude your response is perfectly spot on. Funny you mention all you did because yes, I'm running Wilwoods and as I'm sure you know, they've got 4 total bleed screws each caliper but you only bleed the two "highest" screws, which I did 3 times so far. And while I'll do another 1-2 bleed efforts, I preemptively set an appointment on Wednesday afternoon with a shop in Moab to vacuum bleed the system if I still can't get it.
And then separately, you're spot on regarding the caster - I called PSC today and they told me the same thing. I'll check to be sure but I think I'm at 6-degrees caster right now. PSC recommended increasing it, which I will do.
And then yes, the upper ball joint hex head is literally the first thing on my tool packing list!
Thank you for the foresight on greasing the ujoints. I did so already but I'll keep an eye on it. I don't think I'll need to shorten the upper bolt; I've got about a quarter in clearance between it and the axle shaft yoke.