2) I'm pretty sure the initial JVM was a clone / extension of a Smalltalk VM. Having trouble googling the details, but while you may be having trouble getting it to work on your particular Windows install you might want to consider that you're possibly ignorant of the fact that the Smalltalk VM is not only one of the best available but battle tested over decades.
I would guess that what you're seeing is a particular windows issue that has nothing to do with the VM itself.
I did, yes I know that Smalltalk needed a VM, Pharo == smalltalk, and the like.
Wikipedia for Pharo says they have a VM with JIT, etc. I have never heard a peep about the Smalltalk VM in any circumstance as a performant target for any language. Ever.
If it's battle tested and great, why isn't it used for anything else than Smalltalk ports? Is there a python, ruby, javascript, java, etc port to the smalltalk VM?
If it sounds like I'm being dismissive, that's not the point. The point is the Smalltalk ecosystem, like Lisp derivatives, likes to have its own top-to-bottom stack completely isolated from "real" execution platforms.
For Lisp it's so bad that Clojure is rejected by some Lisp purists because it can JVM / JS compile.
IMO, for example, Ruby made a strategic error writing their own VM rather than just embracing the JVM as the main VM, although when Ruby was writing their VM invokedynamic hadn't been added to the JVM. Well, and they should have added some optional typing.
1) YES smalltalk _has_ been ported to the JVM https://www.redline.st/ AND you can also run it in the GraalVM https://www.graalvm.org/
2) I'm pretty sure the initial JVM was a clone / extension of a Smalltalk VM. Having trouble googling the details, but while you may be having trouble getting it to work on your particular Windows install you might want to consider that you're possibly ignorant of the fact that the Smalltalk VM is not only one of the best available but battle tested over decades.
I would guess that what you're seeing is a particular windows issue that has nothing to do with the VM itself.