fwiw I think Perl was so popular in the late 90s that a transition like Python2.0 to 3.0 that traded some backward compatibility for some structure COULD have been successful. However, the Perl community also got tired of waiting such a long time for what is now Raku, and it was so different with no incremental migration path, that the lifeboat never materialized. Its not like Larry and the community didn't know that a transition was needed, but the execution was not there.
> a transition like Python2.0 to 3.0 that traded some backward compatibility for some structure COULD have been successful.
I think Perl was a lot further away than Python was from anything that would have allowed "trading some backward compatibility for some structure".
This was a clear case of a language collapsing under the weight of its own poor decisions and lack of coherent design. Could it have been kept on life support with a series of incremental improvements? Probably, but things wouldn't have gotten materially better for its users, and it would have bled users anyway as the industry left it behind.