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I played around with the SS box, trying the separate the the piece to which the suede is attached from the outer piece. I could move the edges a bit, but the bottom must be glued down really well.
If I could separate that piece, it would just take drilling a few carefully-sized holes into the plastic.
To go all-out, I could rig some adaptor to go from the male end of the watch charger cord to a female lightning port.
 

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