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Aye. I'm fairly sure the actual duct entrance is the chokepoint. Any reason not to strip the outer of the dynamo cable off? The two inners have plastic wrap round them anyway, but if I can cut away the outer it'd make it a bit smaller.
I will be using a framebag for only for huge distances/the TCR - not every day.
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I would not strip the cable off. If it fails because it rubs on something or your stripping job is sub-par you're up shit creek. It will be more durable and easier to adjust if required outside the frame. The only reason I put mine inside the frame is it was super easy to do so with the big frame ports. My fork cables are just covered with electrical tape and have been fine.
Depends how big the cable guide is. Might be too small a diam. to allow it through. Could just electrical tape it along the bottom edge of the top tube, that's neat enough. If you use a framebag it'll be mostly covered anyway.