If it wont work with VS the Eclipse CDT (C/C++ Development Tooling) may be another option if you look for an IDE instead of the command line.
It works well with makefiles of any kind and is easy to use with GCC/MingW on Windows.
http://www.eclipse.org/downloads (69MB download + local installed Java)
Havent tried to compile/debug Squeak with it but should work out of the box.
Bye Torsten
vm-dev@lists.squeakfoundation.org