TokenVariants VS foundryvtt-magic-items

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)

FoundryVTT Magic Items - This module for Foundry VTT and specific for the DnD5e system, adds the ability to create magical items with spells or feats that belong to the item itself, such as staffs or magic wands, which will be automatically inherited from the character who owns the item.

Magic Items - Allows adding additional spells and such onto magic items directly. Very useful for items that function on charge systems that can be upcast, though a little tricky to work with.

Well there's your problem right there.

Magic Items might help you. I believe you can set it to use multiple charges and scale with number of charges.

a solution could be to code your cutom "feature" into custom magic spells and use the mod "magic items" which let you add spells to magic items with customizable charge cost per spell, number of charges, charges regained at x and so on

What you want is the Magic Items Module... it works with MIDI-QOL and DAE. https://gitlab.com/riccisi/foundryvtt-magic-items

Magic Items

There's an issue for this raised on the module's gitlab page: https://gitlab.com/riccisi/foundryvtt-magic-items/-/issues/82