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Stealing my ideas, the bastard!
I've not done it, I was just thinking about it. Bit annoying the Tripster doesn't have those cable holes like the 4S. I thought about running a battery rear light but I love not having to think about charging batteries so I don't want to lose my rear light.
Ooh, another option would be to run it via downtube and then out the Di2 FD cable hole and up the seattube to the light. It would then be hidden by the mudguard (if I had one).
Since the Tripster doesn't have the toptube cutouts, I was thinking about this problem recently.
What about running it via downtube, up seattube and then out the seatpost somehow (either open top under saddle or with hole drilled below clamp but above frame, ie. in the frame slot?