foundry-filepicker-favorites VS FVTT-TokenHUDWildcard

the module filepicker improvements can let you add some pre definited folders to the folder tab on the file picker so you can easily set where to upload with a single click

Moulinette (specifically Moulinette Core + probably Moulinette Scanes, Tiles, and Image Search given what you mention). It provides an experience more similar to what you're describing to look for assets. I'm too finicky about my file compression to personally use it much - I'm a Filepicker Improvements stan myself as its ability to favorites to the filepicker suites me well - but a lot of folks love Moulinette for the experience you're after.

I'm personally a Filepicker Improvements fan, but a lot of people love bigger overhauls like Moulinette's search options or Alpha Suit's file manager. There's also folks that prefer just working from their own files/internet and go Drag Upload.

Filepicker Improvements - Lets you favorite folders for quick access when selecting token images.

Filepicker Improvements

If you haven't, you can try this fix for "Token HUD Wildcard" https://github.com/javieros105/FVTT-TokenHUDWildcard/issues/36 which uses the wildcard feature but there's a button when you right click on the token that shows what token image to swap to.

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.

You might want to check out the v9 compatibility thread on the GitHub page for Token Variant Hub. It looks like the TVH is compatible with v9 now, but lost full functionality, which should be fixed in FoundryVTT v10.

There's a module called Token HUD Wildcard that can add a little icon menu to the token HUD displaying whatever matches it finds for the wildcard images. So if you name your files in a certain way and put them in the same folder, you could make a few tokens called Daelkyr_1, Daelkyr_2, etc. and then be able to switch between them easily.

see the first image on Token Hud Wildcard for an example

Token HUD Wildcard

For convenience use https://github.com/javieros105/FVTT-TokenHUDWildcard to switch between images.

"It would be so cool to use my Streamdeck to interact with Foundry." -There's a module for that. "What if difficult terrain was automatically calculated?" -There's a module for that. "I wish my players could change their token for when they're sitting." -TAMFT. It's just crazy.

Token HUD Wildcard for adding a button to the token HUD that accesses that token's Wildcard image options. Basically, it makes it easier to swap token images for your shapeshifting creatures, or for those players that often use Disguise Self.