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@BringMeMyFix
Definitely some optical weirdness going on in the first photo.
Interesting to see how Cannondale have got it set up on their website - definitely more like what's being recommended:
Looks like moving from the 54 to the 56 will be perfect - only 1.5cm more in the length, but a slightly more relaxed seat-tube angle. Chances are you won't even have to swap for a 10mm shorter stem, with a bit of judicious saddle/bar/hoods jiggery-pokery.
I think the sizing on the Bowery is a bit of a red herring. They're trying to fit huge swathes of the population onto a handful of sizes. Obviously the whole compact frame/aheadset/post-mtb-scene-seatpost era helps with that, but it's always going to be a compromise.
I vividly remember the 90s, and the general trend for 'smallest size that's rideable' - did it myself - but in the long run, I've definitely reverted to the larger frame camp. The frame's something to hang the wheels and contact points from. It's the heart of the bike, and designers/builders go to great lengths to imbue their products with certain ride characteristics; and I think that as you move contact points further away from 'the heart', you water down those characteristics.