Hi there,
Are you familiar with Texture Painting with stencils? Your plane needs to have UV unwrapped done in an external 3D Modeling application.
Texture Painting in Blender for Absolute Beginners - YouTube
Texture Paint with Images - Stencil Brush (Blender Tutorial) - YouTube
Blender 2.8 Texture Painting Tutorial: Stencil and Alpha Mask - YouTube
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