Hi Charles,
Ok it’s definitely on right! 
The reason I asked is that you mentioned you had replaced the winding wheel with another. Winding shouldn’t get harder when you tighten the screw.
A few things you could check if you haven’t already would be:
Does the new wheel have a small counter bore on the underside? I believe it should be perfectly flat (no counter bore or recess) and just make contact with the shoulder on the arbor when placed over the square without putting pressure on the bottom of the seat in the bridge when tightened down.
Is the click spring set all the way down in it’s recess and sitting below the bridge surface?
When looking from an edge view Is the underside of the bridge flush with the pillar plate? Burrs or small screws sticking through the plate can sometimes keep bridges from seating flush.
As for the sleeve…I checked the hardness of one and it wasn’t as hard as I thought it would be. It does seem possible that a small easy-out could get a bite and just might work as you suggested. If it is too hard and breaks it apart then that too might be good since you’re going to replace it anyway. Another option is to dissolve it out by soaking the pendant with something like Sparex or another corrosive that would dissolve the steel sleeve while leaving the brass unharmed. If the threads are a real mess then in most cases running a tap back into the pendant will restore the threads well enough to hold and adjust the sleeve.
Please keep us posted and let us know how things turn out Charles,
Bob