EDIT: switched to a better example, and clarified why this is a real problem.
I\'d like to write unit tests in Python that continue executing when an assertion fails
I realize this question was asked literally years ago, but there are now (at least) two Python packages that allow you to do this.
One is softest: https://pypi.org/project/softest/
The other is Python-Delayed-Assert: https://github.com/pr4bh4sh/python-delayed-assert
I haven't used either, but they look pretty similar to me.