1. I'm not 100% sure regarding Crossvover, but typically with any virtual machine software, you need to map the virtual USB ports to the physical USB ports in order to get this working.
Otherwise, the virtual environment for Windows will map the driver to a USB port that doesn't really exist on the hardware side of things.
2. Crossover is based on the WINE code which does not work with Spooky.
Crossover is actually not a Virtual Machine. If you want to run a Virtual Machine you will have to use VirtualBox.
There are instructions titled, "Spooky2 in Linux or Mac 17 Aug 2014" on http://www.spooky2.com/downloadsPage/
For more details, please check the link: