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And even before this is accepted and in 3.9, doing this in the tooltips would make things a lot easier to read (so much less nesting). Though I'm not sure how far the tooltips should diverge from the actual code you have to type out.
I've implemented support for PEP 604, but I've left the tooltips to use the old Union[] and Optional[] notation for now. It's a two-line change if we decide to change it.
https://www.python.org/dev/peps/pep-0604/
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