I use SwordSearcher 8.3 and really love it. I also have an iMac and a Microsoft Surface Pro. However, my Surface computer has a really small screen. What I did is to install the Microsoft Remote Desktop app from the Mac Store and then connect remotely to my Surface, which gives me a much bigger screen to work with. That works great for me and uses very minimal memory on my iMac, around 200-300 MBytes of memory, as opposed to several gigabytes of memory if running a virtualization app like VirtualBox, Parallels, or VMWare. I also use CrossOver and can run SwordSearcher directly on my iMac, but I find that takes more memory than if I were to connect remotely to my Surface. My iMac has only 8GB of memory, so memory is at a premium. I had wanted to upgrade to 32GB of memory recently, but when my repair shop told me they were required to use Apple memory, and it would cost me about $900, I gave up on that option. Using CrossOver runs pretty good, but with the next release of the MacOS (Catalina), my version of CrossOver will no longer work since MacOS Catalina has dropped support for 32-bit applications altogether. The developers of CrossOver are hopeful for an upgrade that will enable SwordSearcher to run on Cataline, I am not holding my breath on that.
Just thought I'd give my two-cents on this subject.