Hi @DylanWright
To fulfill your requirement you have to create two Shopify store 1 for retail and second for wholesale.
Since stores are different you will able to customise the feature as requested separately.
Now about data and images if you are aware of bulk upload and Excel you can manage this by your own.
For this you have to create two different Excel having the same information except the image and description.
Or you can hire someone who can build a custom APP for you where you will upload images, product description, price etc.
And APP will sync retail data to retail Shopify store and wholesale data to wholesale store.
By this you add and update data at one location and data will be shared to both stores.
Hope this will help…