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I was thinking SRAM Doubletap would work - you drop the post on the first click (outer ring) then shift it back through to the the start (lower ring).
There are 27.2mm posts about... cable routing would be difficult though, I agree.
Not going to do it (I'd want a dropper for my MTB before I start messing around with one for road), just curious
Could one convert a road bike to 1x (say 50t/10-40) and then use the spare left-hand front shifter paddle to operate a dropper post? How much cable pull is required to operate a dropper post? Is this something pros might do eventually? Has anyone got a spare dropper post/bike who could give it a go? Seems like it would be great on gravel/CX stuff.