Argument about an underground drain in Vienna

I see no problem with this. These will also be rendered accordingly. See Way: 315219370 | OpenStreetMap

You are correct, but this map style is now the ubiquitous “standard” on osm.org
But you can compare many other map styles and you will notice the same effect. A waterway that visually crosses a path/street unobstructed, looks like a level connection of both paths, no matter what map style.
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It seems not be a problem with tunnel=flooded. Here is one which renders correctly as dashed line: Way: ‪Bachüberleitung Fasulbach und Rosanna‬ (‪1183699176‬) | OpenStreetMap
Or this one: Way: ‪Hochkopfstollen, part of Rißbachstollen‬ (‪343939314‬) | OpenStreetMap
I only guess that it’s because of waterway=canal instead of waterway=stream.