Will US stores transfer small leather goods?

Yes. But the rules can change with the wind.

My recent experience is that if a product is new (like a new color) and in demand, they may have to wait 30 days before it can be transferred. But this is not always the case.
 
Will stores transfer items from a category that they don't sell? I want to buy an Apple Watch band but the store my SA works for doesn't carry the Apple Watch category at all (another Hermes in the same town does). I just scored a Birkin from my SA so I don't want to shop elsewhere. Thoughts?
 
Anything and everything can be transferred between boutiques. They can also trade items with each other to move inventory around. It just depends on which boutiques are "friendly" with each other.
My SA talked about this and she mentioned that while the NY Madison has the highest likelihood of availability of items, they are not the easiest to convince when it comes to transferring (any) items.
 
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