User File Upload with custom meta data fields

Hi Everyone,

I am a PHP developer who is very new to WordPress and I have no idea about how to accomplish the following.

I need to build an upload page so that some contributors can upload files along with some metadata and a list to view the uploaded files according to the metadata fields. Example The user will upload fileA.doc with a level 2 difficulty [difficulty = 2].

An admin of the site has to be able to add in multiple metadata fields to the form without changing any of the code. Is there any how-tos or plug-ins to accomplish something like this?

We use gravity forms which has a similar function but will only upload posts with attachements that have metadata attached. Sorry if this is confusing I don’t really know how to explain it much better.

Thanks!