@ebidel did you ever come to a conclusion/solution. I too am feeling the same problem, stemming from our test framework that uses css/xpath selectors.
I've been toying with the idea of doing something similar to
`querySelectorShadow('my-app my-component my-other #button')` but as you indicated it requires you to know about the shadow root structure, not ideal for end to end tests, would make them very brittle and hard to write.
Because this issue is so annoying, we've even developed a custom mixin behavior that lets you "automate" behavior of a component, and you trigger it via attributes
e.g. <my-component automation-on="true" automation-action="run_search hello world">
We have a series of keywords like "run_search" to simulate high level actions on our components, which just do things like click buttons in shadow roots. Whilst cool, this really isn't practical.
Asked all over the web, from selenium forums, to web driver, to here and polymer slack, seems not many people care about the issue of being able to easily interact with elements in a shadow root :( 👎
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