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I think it would be trivial. Both watches are paired but only one is tethered and active at any one time.

When you switch, the new watch is tethered and updated, and the inactive watch untethered. Simple.

This could be user-initiated but say a "make active" button or simply automatic when a watch is put on.

Simple.

I think it was left out of the first release because it makes the interface more complicated in order to serve a truly tiny number of users. I fully expect this feature to be added soon.

I wonder if its more of a iOS/Watch app feature, than part of Watch OS? The ability to quickly swap between paired watches in the app (if you put on the wrong one, perhaps a popup on your iphone to say "this apple watch isn't your active watch. do you want to make this watch active?" opening the app up, or something) - it could be so easy if apple wanted to make it so.
 
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