OP: since you're in NYC, I'd say drop by the C&J store on 56th and try the Weymouth. Even though it's on an E, I find that it fits more generously than say, their 348 (which the wholecut Alex is on). You might be surprised and the leather is amazing. Wearing them right now actually:
These and my AS are hands down better than my C&J BG Alex.
^ Good stuff. I really like the Weymouth, but now that I think about it, I think I prefer the plain toe of the Carmina shoe over the medallion on the Weymouth. I work in finance and the medallion just looks less formal for the office. I still like it, though, and would love to own a wholecut pair of shoes with medallions somewhere down the line.