Maybe I'm missing something but it seems that running Windows on modern Apple hardware with Vagrant is still an open problem.

The most active Vagrant Windows maintainer is Gusztáv Varga(gusztavvargadr)[1] I opened an issue in gusztavvargadr/packer [2] where I discuss my findings.

Maybe someone has better idea how to approach it.

Also, Microsoft archived their Vagrant provider [3] claiming they do not have resources to maintain it which is quite odd.

[1] https://app.vagrantup.com/gusztavvargadr [2] https://github.com/gusztavvargadr/packer/issues/414 [3] https://github.com/Azure/vagrant-azure