Can I display different content based on the user’s past purchase history?

Absolutely.
If you are using WooCommerce or Easy Digital Downloads, you can leverage If-So to display dynamic content based on the user’s previously purchased products.
To learn more:

• The If-So & WooCommerce Integration.
• The If-So & Easy Digital Downloads Integration.
• For other e-commerce plugins, our Custom User Profile Fields Extension provides a solution.