I missed an important point in this scenario.
The "path"option doesn't produce unique paths.

/apps/myapp/homepage/header/highlight/highlight.jpg.esp

could be a produced by resolving:
/content/myapp/homepage/header.highlight.jpg
as well as by resolving:
/content/myapp/homepage/header/highlight.jpg

Therefore  it should be up to the contenthierarchy to define these
hierarchical structures.

So dots should remain dots.

Regards,
Dominik

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