It's really cool how much of this feels familiar to me from my own experience building and evolving bootstrapped systems

(1997)

It's really a shame that the early history of Smalltalk-80 was such that it remained too locked up in licensing and $$ implementations and so didn't get a broader penetration. That and it was about a generation or two ahead of the extant microcomputing hardware at the time, so wasn't going to be shippable in a performant way on a general consumer class machine even by the time the Lisa and Mac shipped in the mid-80s.

I was very excited by Squeak in the late 90s (and even more excited by Self), but it was clear that the time of Smalltalk being able to make any kind of broader splash was done, and Java was where people's attention switched.

Imagine if a consumer focused machine like the Macintosh had shipped, but based fully on Smalltalk, with an authoring environment built on it for "regular people". The closest we got to this was Hypercard.