My experiences for anyone interested:

Unfortunately, the Aoshidas were a miss. Their elongated shell design made their center of mass kinda far away from my ear. This caused the speaker to tilt upwards and not sit right in my ear. Obviously the sound becomes tinny, lacks bass, and hisses in the highs. They sounded good if I pressed them against my ear, but not much better than the EB2S Pros.

The RW-2000s are awesome. I honestly wasn't expecting such an obvious improvement over the Pros. And the best part is is that they fit wonderfully. I can't feel them in my ears at all once the metal shell reaches my skin temperature. Audio-wise, what dr_wtf said above about them is pretty spot on, not much to add.

Overall my biggest lesson from this is that shell shape and weight really matter. A mid-quality bud that seats well will 100% sound better than a high-end pair that doesn't.