I had a lot of the same issues and finally started to enjoy using smalltalk once I just gave up on the idea I was going to use it for anything practical. After

I had a lot of the same issues and finally started to enjoy using smalltalk once I just gave up on the idea I was going to use it for anything practical. After that I found squeak to be just fine to play around with. From my perspective as someone learning about it post 2015 is that the really killer “feature” is the ability to modify anything anywhere while the image is running. But this is also the feature that makes it so impractical. You start to realize as you are tinkering how simple and elegant it is and how much modern tooling really gets in the way. But this is all based on it being built up upon itself and all the magic of this sits in an environment that’s so foreign to other tools it always feels awkward to interface with them.