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Certainly possible, but the Di2 wire is tiny. By the time you've hearshrunk it to a brake hose/cable it virtually disappears. Even on my bike with a straight 1 1/8" steerer and lugs, the Di2 wire is barely visible. You don't need a 44mm headtube for that.
Brommers-
No, you're right. I'm having the 44mm HT anyway because tapered forks and I've had the tubing in a box at home already for 6 months so that's what I'll be using.
I've seen the wire ran along the brake hose on several builds but it just doesn't do it for me. Looks like a bodge (so is drilling a hole in your fork but at least it's invisible) and since I'm starting from scratch, I might as well try something more elaborate
PhilDAS
Yeah I mean accepting the fact that the hoses will have to be external but hiding the di2 through the steerer