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Files can be added after you create an item. Files, screenshots and logs are separated items that belong to a single download item. This means that you can upload several file types (for versions, platforms, etc.) for a sinlge download item.
About error... please update to rmcommon RC and check if problem is solved. Also you can check your server error log... maybe this file can provide more ifnromation about error and we can fix it.
Thanks.