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OK, after a bit of experimentation, it appears both 3.2 and 3.3 eventually get annoyed if you mess about too much with __pycache__.
1. They're both fine if __pycache__ is entirely unwritable (they just silently skip caching the bytecode)
2. 3.2 throws EOFError if you replace the cache entry with an empty file, 3.3 silently rewrites it with a valid cached version
3. 3.2 throws EOFError if you replace the cache entry with a directory, 3.3 throws a more accurate IsADirectory error
That means my chosen test case is a valid one, and I can just update the offending call in importlib._bootrap to use the new frame stripping hook as I originally planned.