Ok, I've been testing further, and if I compile and load an example plugin into Ableton and then remove it, I'm able to delete it from Explorer, meaning the compiler is able to overwrite it with a new build, so you should be ok if you've got Live Lite available to you and aren't averse to using that instead for testing.
My own plugin is seemingly held by Ableton after it's been removed from the project. No idea what's caused it, but even wiping and reinstalling Ableton and completely restarting my project with a blank template from duplicate.py with the same name doesn't fix it! Seemed to happen after a few crashes, so wondering if there's some crash protection keeping watch on it now... very bizarre.
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