Do you so it over PGP? Or is it done with ZAE like with Proton?

I think at least the first one kind-of exists, but I haven’t tried Tiny11 so it really couldn’t say if it does; at the very least it shows that Windows ISOs can be modified.

It’s probably be more of a pain now than ever, since Apple is now using their own proprietary chips.

This is why non-libre software sucks. They have 0 incentive to not screw you over.