Well, I don't think Tim's point stands anyway. It assumes a blank OS on any machine can use configure and cmake, but not squeak. Can windows machines run configure and cmake out of the box?
Some sort of installation hurdle must be overcome, whether cygwin or new-squeak-based-builder.
People who are building VM's are a much smaller, more-technically capable group than those who need to deploy something (e.g., an application). If you design your deployment system for the former, it think it won't be useful to the latter.