No idea about newer versions of Windows, but Outpost 2 runs just fine under wine using a 64-bit install of Ubuntu.
I tried firing up a VM about this, but my low end laptop basically ran out of memory and locked up. Oddly, the VM ran, and I was able to shut down the VM, but it never restored my desktop. Everything outside the VM was completely unresponsive. I had to hold the power button down to turn off my laptop.