Up and running with Vagrant, VirtualBox and the Puppet Debugging Kit on Windows.
Running the Puppet Debugging Kit on Windows is fairly straightforward, in that the setup process is nearly identical to setup on OSX and Linux.
However, the typical "Vagrant on Windows" caveats apply.
I've attempted to cover the entire setup process here, going from a system with no virtualization tools installed, to a working Vagrant + Oscar + Puppet Debugging Kit environment