Sync up Pictures from ipad, mobile devices, notebook to a category page on our website

Picture Project We have a brand new website called [login to view URL] using wordpress, woocommerse & a Puca theme. We have tens of thousand of products in 3 different locations, and some of the products are new & used & go back up to 10 years old, so we do not have product descriptions, so our plan is to use the thousands of pictures we have on our ipad, notebook, and mobile device android/iphone, and upload the picture to our website and sync it automatically in to a category page and we want to add many pictures to a category page. On these devices we will have the pictures in different folders so we know where to sync up the pics on the category page on our website. Another task is these pictures are very large pixel size and they have to be resized before synced up so they do not slow down the website! And this process has to be fast & not take forever to sync, yes I know it depends on the internet speed also. We need this project done asap!, you need to keep me informed everystep of the way, you must speak English, If you can use skype with me, that would be a major plus! If you have done a project similar to this, thats a plus, let me know about it. Also any code changes that are made in the backend have to be put in to a text file for me, the file name & directory, so I can find where the code changes were made. Also any code changes, cannot interfere with any wordpress , woocommerce, theme or other plugins because we do not want to have to update your code changes everytime we do an update.