Are there specific annoyances associated with quoting always, apart from the 2 more characters?
Yes. Since the quoted strings aren't parsed by Python, syntax errors in these strings go undetected until somebody does parse them (e.g. your static type analyzer). Having the Python compiler de-compile them back into strings means they got successfully parsed. Though this doesn't rule out other errors, e.g. NameError.
I thought this was discussed in PEP 563, but now I can't find it,
so unfortunately I can't steer you towards any more info on the