Item Tooltip
Configuration
Image files
Create the required files into contents/test_tooltip/textures/tooltip/
.

Run /iazip
and then get the item ingame.

Old method
You can add custom textured tooltips for your items, please refer to this example addon: https://www.spigotmc.org/resources/items-custom-tooltip-texture-example-itemsadder-addon.87883/.

Limitations
You cannot show custom enchants as they will go out of the window if the image is too small.
You have to write everything in the tooltip image, text would go out of the window if the image is too small.
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