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You can run any python script with calibre like this:
calibre-debug path/to/script.py
As for GUI, since DiapDealer has calibre versions of his plugins, presumably, it should not be hard to adapt to using PyQt instead of Tk.
On a personal note, I recommend you guys bundle python, at least on windows. It will make life a lot easier for your users.
And even on linux and os x there are no guarantees of the python environment available. What python libraries are present and what are not. For instance, on my Gentoo system I dont typically have the python Tk bindings installed. Not to mention the whole problem of python 2 vs 3. Different linux distros may or may not have either python 2 or 3. And since Sigil already distributes the Qt DLLs, it should be relatively easy to also distribute the PyQt bindings.
Then you can provide a consistent, platform independent python environment for your plugin developers and ease of use for your users.
While the goal of having the plugins work with any scripting language is laudable, that doesn't mean you cannot have a single, favored language.
Anyway, that is my opinion.
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