browse and upload button under a particular category

Hi All,

I am creating my website using this cool open source, I want to provide a browse and upload button under one of the category on my website, i.e. when anyone click on a particular category lets say "list" then there should be one upload button through which any user can upload an image or a pdf file, which can be added to the cart and can be checked out.

example- I want to buy groceries, but i dont want to select all the items one by one on website, rather I've list of all the items which i want, i just want to click an image of the list and upload it and i should be able to checkout with that image of the list.

please suggest.
Thanks

A rather Custom Demand, and cannot be done, by default OC, or a Mod, I'm aware of. You need to get a Pro, but I guess, it's gonna be a heavy load, time- and money-wise, trying to make your dream come true.
Good Luck
Ernie
bigmax.ch/shop