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Not trying to derail your approach, but the issue isn't whether you need a 50/11, as much as whether you like riding a 50 x 13,14,15,16,17,18,19,21 etc. Those are the gears that determine whether a 50 is right for you. Similarly, your 34 may be used mostly with your 12, 13, 14, and so on.
I've ridden a couple bikes with the Wickwerks adapter. On both it barely works with a 44 front ring. It does throw in a little bit of flexibility into the shifting system, not enough to really feel it with manual shifting but definitely with Di2.
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