This should let you do it: https://docs.shopify.com/manual/configuration/store-customization/communicating-with-customers/obtai...
Let me know if you need anything else. I would be glad to provide my services if you need any help setting up your store. Just e-mail me at michael82605 (at) gmail (dot) com. If you would like, I'd be happy to set up a free Skype consultation.
Definitely it is possible to configure upload files for products into your Shopify Store and the best part is that you would not have to do it for each separately, it can be coded once and can be applied to all pages on the site to simply the integration part.
If you need any assistance, feel free to ask for it.