This is awesome, shared it with another DM friend of mine to scope. This works incredibly well and I'm kind of amazed with how many options you have.
I know you said it's a soft alpha, but the jester hat's color change seems to only affect the front-facing triangle. Not sure if this is intentional, but figured I'd point it out since you have an insane number of items and I'm sure it's hard to catch errors :)