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I mean I like the sound of that, but it seems the long way round to get there. Plus I'm not really up for drilling. I think either the Di2 under the TT or a wrap around @gillies is right, I think there should be space under the frame pump as the pump contact points are very near the joints and with my Zefal there is a nice amount of room between the pump and TT. Maybe @gillies pictures and my experimentation will help you decide....
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?