How to automatically add category to front page, and when clicked, display custom post type posts of that category

I have a bit of a problem, been looking at various answers and still can’t quite get it. Here’s the problem:

My client would like to be able to create new categories for her Custom Post Type of ‘Artwork’. When she creates it, I want the first Artwork associated with that category to show up on a page that also has the first Artwork for a different category.

I need to write a loop on this front page that grabs all categories, and displays the first post associated with it. When you click that post, it goes to that category archive page. When a new category is created, it automatically adds that first post to the grid of others.

We are working with a custom post type. Thank you for any help or insight

Esteban

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