I've been at ESUG a few years ago. I can definitely recommend it if you want access to all kinds of Smalltalk and Pharo experts, and listen to all kinds of topics that contain a high amount of expertise.
I remember that I wanted a visual step by step debugger for a visualization library [1]. I was lucky enough to find the library maintainer himself. He liked the idea, and within just 30 to 60 minutes we programmed a prototype in (this was around ChatGPT 3.5, so pure hand coding).