I just tested this on my server:
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$ mkdir -p Testing/If/Subsonic/Goes/This/Many/Directories/Down
mkdir: created directory `Testing'
mkdir: created directory `Testing/If'
mkdir: created directory `Testing/If/Subsonic'
mkdir: created directory `Testing/If/Subsonic/Goes'
mkdir: created directory `Testing/If/Subsonic/Goes/This'
mkdir: created directory `Testing/If/Subsonic/Goes/This/Many'
mkdir: created directory `Testing/If/Subsonic/Goes/This/Many/Directories'
mkdir: created directory `Testing/If/Subsonic/Goes/This/Many/Directories/Down'
$ cp Toto/Toto\ IV/10-Toto-Toto\ IV-Africa.mp3 Testing/If/Subsonic/Goes/This/Many/Directories/Down/
Updated the search index and reloaded my left hand pane...
'Testing' appears as the artist under 'T'. Clicking on it I get 'If' in the main panel, with the option to keep clicking down till I get:
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Testing » If » Subsonic » Goes » This » Many » Directories » Down
and the track I copied there is displayed. I also verified that searching for this song via the search box in the top panel, found the file.