Re: Comparison with Python isn't really fair
The library issue was a key problem, which is why the PSF sponsored some ports, but even then adoption was hindered for a long time (until Python 3.5) because Python 3 used more memory and was slower for many things and didn't offer anything new. That was never going to help overcome software maintenance inertia.
But I think that, in the end, we learned from the experience as can be evinced by the vastly improved release process.
I personally don't know of many libraries that transpile, though I'm sure there are some. For most developers without C-extensions six or something similar and universal support for u'' and b'' prefixes was enough. Certainly less work than, say, switching from unittest to pytest.