TokenVariants VS dfreds-droppables

The Token Variant Art module can handle this (scroll down to Image to User Mappings). You'll probably need to write some macros to change things on the fly though.

Token Variant Art - Makes it possible for a token to have purely visual token variations. Better than Wildcard since it isn't forced to be random. Very unintuitive to work with however.

There is a short clip under this release: https://github.com/Aedif/TokenVariants/releases/tag/2.14.0

if you want more control with your wildcarded tokens there are a few modules that can help, for example token hud wildcard will add a simple right click menu to a token to chose which image to use (not officially updated to v10 but it should work), token variant art will give you A LOT more options about using multiple images on a token, even different images for different players if you want.

I used Token Variant Art for this... it is pretty nice and maintained. I have worked with Aedif and he has made enhancements to the module recently. https://github.com/Aedif/TokenVariants

There is also a not fully automatic , but still very useful feature on Token variant art module https://github.com/Aedif/TokenVariants .

Token Variant Art (only really active when I'm preparing the game)

dfreds-droppables - DFreds Droppables is a FoundryVTT module which allows you to drag and drop an entire folder of tokens or journal entries onto the canvas.

DFred's Droppables - Allows for dropping a whole folder of tokens onto the canvas. Useful for spawning the entire player party on a map.

DFreds Droppables