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"One example of a wart is that I can use a Wax Font object in SetFont, but I will get a wx.Font back from GetFont."
Have you considered that wx.Font could be adapted to Font?
While I share some of your distaste for many of the neocodisms dumped into Python recently, I'd encourage you to investigate the use of interfaces and adaptation for wax.
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"""Have you considered that wx.Font could be adapted to Font?"""
Yes, but I'm not sure how to do it yet...
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Scratch that. I just added some code that gives all widgets that inherit from WaxObject a custom GetFont, that returns a Wax Font instance rather than a wx.Font.
I will probably need to refactor this code once I need more methods like this.