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Maybe it goes in error at starting, after the rough initialization. Try to start calibre or editor in a terminal and see the output. You can also put some debug msgs in your plugin (a print() will be shown in the terminal output) to see if it loads completely, or where it aborts if it's the case.
Well, I won't learn you how to debug, I suppose you already know all that.
A tip : if you change your code, no need to reinstall the plugin, just update the zip and restart calibre or editor.
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