If you are willing to move up to macOS 10.12, I know for a fact all of Qt 5.12.5 (the long term support version of Qt) will build on macOS including full Qtwebkit. I doubt there are any Qt 5.13 specific features in Calibre that do not exist in Qt 5.12.5. Python 2.7.x should build as will Python 3.7.2 with macOS 10.12.
I regularly build all of these against the macOS 10.14 sdk with the minimum deployment version set for macOS 10.12.
FWIW, Qt 5.11.x will build against macOS 10.11 but not Qt5.12.x due to changes in QtWebEngine and QtBase that were introduced in Qt 5.12.0
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