Trufit and Tilia Giffin can do this already (both same software, onyx is using tilia griffin engine)
not sure about adding extra bleed though. waiting for my trial licence to test them both out.
Not quite there yet, I've looked at those and they would still require a customer supplied file to be cleaned up in photoshop/illustrator, background removed etc. In most cases.
I'm talking about a customer sends a picture of their dog sitting in grass and wants cut out stickers of the dog.
Or a customer sends 3" x 3" yellow star in a letter size PDF file, still requires manual cropping now. should'nt be too hard for ai to figure out
The ai software could be trained by feeding it previous job before / afters files
I was considering truefit/tillia but the types of files I get from customers would still require the file to be prepped in illustrator and if we're opening the file in Illy any way might as well add the cut line etc there.
The nesting feature of true fit looks really good though, wish they'd just make that built into onyx instead of having to jump through different software windows