Hi @dabeecher,
This is certainly possible using Premium Templates. This extension includes a customizer that allows you to tailor your PDF documents using product columns and total rows blocks, as well as custom blocks that you can place in different areas of the document (currently 20 different ones) and display based on given conditions (order status, payment method, billing or shipping country, etc).
The customizer also allows you to sort items by product name, SKU, and category. In addition, Premium Templates provides two additional templates: Business and Modern.
For your specific case, you can use the Thumbnail block:
…and then you will see the product thumbnails in your PDF document, like this:
Please note that, since the rules for the WordPress.org forums doesn’t allow us providing premium support or answering pre-sale questions for paid plugins, please contact us by email to [email protected], if you have further questions.