Regarding Windows on Virtual Machines:
Virtual Box (Oracle) is freeware.
And it is like Plug n Play - easy to use.
(Just don't install 64 bit Windows versions - again just a hunch. But older software (and hardware) might not properly run yet on those.)
But Windows isn't necessary.
Another thought I had: I don't much like the idea of my precious Macbook Pro sitting there with me in the dewy field.
A small Windows laptop nowadays is cheap (300$) and it doesn't have to be fancy for guiding only since image processing would be done on the Mac.