"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.
"""Have you considered that wx.Font could be adapted to Font?"""
Yes, but I'm not sure how to do it yet...
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.