Unfortunately, I mostly just follow the list. My experience is limited to elementary experiments: just defining some classes, and using them in a workspace, using the transcript to inspect the results.
I just don't seem to get it. I think I master the building blocks, I get what is in the SBE book, but somehow, I don't see how to tie the pieces together into something that looks like a regular application.
To be honest, it's more a mystery what keeps pulling me towards Squeak, given my poor results until now.
I am not in a position to answer this question.
Everything is hard, but not annoying. I probably need to get more general knowledge of the 'Object Oriented' paradigm, and some UI design skills. A 30+ year career in mainframe development left me a very procedural guy, and a UI for me has 30 lines with 132 colums each.
What got me interested was reading about Squeaknos, turtles all the way down, at one of those moments I was struggling once more with a linux upgrade that destroyed the GNUstep installation I had managed to install.
Now I see this is miles beyond my reach, but that was the spark.
Currently, I'm trying to build an intelligent doorbell, with Squeak and a Raspberry Pi that was laying around here. Now if only it would just ring outside the simulation.
Did I mention my knowledge of electronics is far below average.....
I don't know if this is of much use to you, but since you asked....