To delete files with just an orange question mark I used command+shift+delete on Mac OS X (El Capitan) 10.11.6 not sure about windows maybe control+shift+delete ?
For the missing files with the orange circle and? Mark you need to go into settings (gear icon) under library+Display and un check "Show iTunes Library" now the orange circle should go away and just be the orange ? Mark and delete it like normal command+shift+delete .
Hope it works & helps you!
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