You've also got to include the pyenv shim instantiation. So now you've got something like
0 0 * * * /path/to/bash/script/to/init/pyenv && /my/path/to/poetry run /my/path/to/python.py -arg1
0 0 * * * /path/to/bash/script/to/init/pyenv && /my/path/to/poetry run /my/path/to/python.py -arg1
0 0 * * * /path/to/interpreter/created/by/poetry/bin/python myscript.py
I seem to recall that with python2.7 that calling bin/python in a virtualenv without activating the virtualenv did not used to "work" (i.e. it would use the system packages). Did this change at some point or is my memory just wrong?
An anecdote: Homebrew uses this method for shipping python executables.
The exception is if your python thingy is "the main thing" running on a server, i.e. your customer facing webapp.
My $.10 anyway
This of course leads to other issues to solve, now that your development environment doesn't actually mirror production.