Will Python 2.7 deprecation effect locally installed?

Does anyone know if the Jan 1 2020 deprecation of Python 2.7 will effect locally installed Galaxy? Also, does the software upgrade to Catalina have any bugs?

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Not until Apple stop supporting Python 2.7, assuming you are using macOS.
Any way it should be pretty easy to port your local Galaxy to Python 3 by replacing the virtual environment that Galaxy uses (by default .venv) with a new one created with virtualenv -p python3 .venv .