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Improve board_with_milestone_spec

What does this MR do?

I manually performed this test and added find's where elements are inserted async and should probably have a find before asserting.

Are there points in the code the reviewer needs to double check?

Why was this MR needed?

Screenshots (if relevant)

Does this MR meet the acceptance criteria?

What are the relevant issue numbers?

Closes https://gitlab.com/gitlab-org/gitlab-ee/issues/1960

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