Recommendations/Ideas Needed – Front end ability to upload images and more

I need ideas and direction figuring out how best to approach my problem without paying for a premium service out of pocket.

The Challenge: I help artists with their websites and online marketing, but most have their own sites and social networks. I have one client who I fully represent and communicating with him and getting content form him is a challenge. He doesn’t have a computer or notepad of any kind. He has an iPhone and that is it. He is not regular on email either. His normal way of communicating is through text. He is also good about posting to his Instagram account. I think he will post directly to a page on his site if I make it super easy and all in one place, preferably with a message thread that we can both see and refer to as well.

I’ve decided I need to make a password protected page on his website so that he can upload his images and add the information along with them. I will be using those uploaded images for a number of purposes (and probably some I don’t yet foresee). Perhaps some sort of user management plugin might work, but geez, I don’t want some big member system set up for one guy.

Ideally, we’ll be able to work on his inventory together. I envision a page where he could upload an image along with 5-10 fields of data for each. I’ve done this using ContactForm7 for other purposes, but it wouldn’t work here because he needs to be able to see all of the entries to add and edit information. He has hundreds of paintings and it will be a painstaking process to get them all photographed, named, with the correct information … and sometimes the information changes (arrgh!)

I do have plans in the near future to create a single website with that kind of functionality where artists can store and manage their inventory, so if any of you know of an existing theme/plugin approach that could work for one guy on his site AND on my site with multiple artists it would be great!

Btw: the site links to a basic site with info just to get it up there. I am currently working on a staging copy using Accesstheme’s ParallaxPro.