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I’ve had the “pleasure” of having to work with Pharo, which is AFAIK based on Smalltalk, and it was one of the most frustrating experiences I ever had with a language. It was a few years ago so the details are blurry, but as far as I remember the idea was that the whole IDE is a basically a VM coded in Pharo that you can edit on the fly, and it was just a mess and super strange to work with.
On the other hand, it was a great learning experience because the OOP smalltalk syntax and way of thinking about your code is different enough to be worth experiencing. But I still can’t imagine a task for which using Pharo would be a good idea, or better than literally any other language.
For my sins I spend a significant part of my time maintaining smalltalk, and it most definitely is not productive.
The syntax is ugly and cumbersome when you start chaining messages. Any advantages the evangelists tout are available in modern languages without the baggage of this dead one.
Today if you want something ‘simple, flexible, interactive’ (interpreted, GC and likely faster) python would almost certainly be a better choice.