Your original question seems geared towards building software from Windows to deploy on the JTK1. The nature of what is required differs depending on whether you are building for kernel space or user space. Because the kernel has no needs for linking to other software this environment is greatly simplified…if you cross-compile user space, then suddenly you need the sysroot files (this is more or less the linker and everything that is linked to along with other tools to do this…it is a subset of the final user space environment).
If you just want to build a kernel, then you may get away with using non-Linaro armhf compilers. Once you need user space the possibility of Windows-based tools goes down rapidly (and quite possibly no such tool chain exists without paying large sums of money). Assuming you do need user space development, and if a VM is your only choice, then perhaps debugging the VM install is the place to start.
I do not personally use a VM, in part because of my system resources being inadequate, but also because the VM frustrations you are running into also frustrate me. There are people here who do use and understand VMs better than me. I suggest that you describe what you are using for your VM, and any kind of setup you have for this…someone who understands VMs may know what is going wrong in your case (or at least have a suggesting of a setting to change).