Wordpress development and management of a large content site

This will be a membership site where users can download videos, plugin's, templates, and etc. The main focus will be videos and will contain all the clickbank categories, Amazon categories, business type categories, and many others. So it will be a very large directory with 100's of categories, and eventually 1000's of individual products members can download.

We need to first determine if this will be set up using a classified, or directory plugin, or just manual pages/posts/etc. Your input in this is very welcome, and I would like to know your thoughts when applying for this job since I am not 100% sure myself which way to go.

We need a membership plugin to use, if you have used one in the past and really know it well let me know.

All products will be loaded into Dropbox, and implemented into the pages (More details on the exact content later).

In the future I would like to have the ability for members to have their own profile pages, and supply us with products to be given away also. Their products will link to their profile where they can sell their services.

There is much that can be done, so if you are a creative thinker, that would be a bonus. If we can really get this going, I am open to paying a percent of the total membership fees, hiring you help, or what ever needs to be done. I have been marketing online since 2001, so I can get traffic, just need the site to be the best it can be.

Please let me know of any questions, and any input on this project.