The macOS Sierra installer should already be open on your Mac. If you quit the installer in order to make a bootable copy, you can restart the installer by opening your /Applications folder and double-clicking the Install macOS Sierra item.

VM typically refers to 'Virtual Machine'. Basically it's a way of being able to run another operating system (Windows / Linux, etc.) without having to reboot and use Bootcamp. I personally use Parallels, which is a popular VM application. In effect, it's like having Windows running on your Mac OS. You can switch back and forth between the two operating systems, like switching between Mac apps. If you have the funds, it's a pretty reliable way of dealing with your problem, it's an actively supported application, as is VMware Fusion (another brand of VM which achieves basically the same thing). Crossover is possibly another option, though I've found that as hard to setup as Wineskin.

My guess is that if it's possible for Wineskin to work with Sierra, it will come along pretty quickly. Other than Linux, the other main use for Wine is basically the Mac OS. Video game emulator raspberry pi. Have you attempted to install FG from the Mac Installer available? Just out of curiosity, when you installed Sierra, did you wipe the hard drive and do a totally clean install?

Or did you 'upgrade' the OS? If you did an upgrade installation, you may just have to uninstall Wine, and re-install. It's possible during the upgrade installation one of the Wine resources got borked. (I don't know very much about this, just saying what I would possibly be trying if I was in your situation) Here's a to how to uninstall Wineskin Winery.