We solved this problem ourselves but I did not get any sympathy from the WG for my "invalid requirements". You probably know this but Apple is `<redacted>` and seems to look on testing with disdain. Quite understandable seeing as their browser is all but meaningless when it comes to Web development but it does end up negatively impacting us.
Its not a simple problem to solve if you want a solution that works in all possible scenarios (like shadow DOM within shadow DOM within shadow DOM...) and you also want to support "unique selectors" (which a testing product needs to be able to do). The shadow piercing combinator ('>>>') could not do this.
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https://github.com/GoogleChrome/puppeteer/issues/858#issuecomment-362840167