Magento File Upload And Attribute Setup – Expert Required

I need a file upload system for Magento. When a customer places an order for a certain product, they must upload a file. (Only jpg, gif, pdf etc)

Also, I need 4 products with 4 attributes set up. For example..

Product 1
Quantity:
250 – £10
500 – £14
1000 – £16

Product 1
Quantity:
100 – £5
200 – £8
400 – £12

etc

If you require any more info, please message me.

Thanks