I can't speak for Glyphs, but I have some first-hand knowledge of this to share. At one of my jobs, we had to do some gaming work which required designers to move most of their work over to PC desktops. Often times, I would have both my Macbook and my PC running side by side, and switching between the two was cumbersome and frustrating so I decided to run macOS in a Virtualbox VM (for things like Sketch, iMessage , and programming... I still do not know if you can even 'ssh' on Windows!).
My PC desktop was, at the time, relatively high-end since the work we were doing was in VR. I had a GTX 980, a modern mobo, i7 CPU – I don't remember the specific model parts, this was in 2014 or 2015. Even with a strong computer like this, and enabling as much direct hardware passthrough as I could sort out via the BIOS software, the Mac VM was nearly unusable on a daily basis. You will need an incredible amount of patience and a high tolerance for random failures. I could simply not do any meaningful work that way.
On the flip side, I have seen the reverse set up working quite well (especially with Boot Camp, if you don't need both OS'es side by side). Some people that I currently work with have Macbook Pros, and external GPUs (I believe also mainly GTX 980s at the moment) Thunderbolted in with the Windows OS getting a direct passthrough. In my observation this setup as been far more stable and productive.
In any case, if I truly had my way, I would simply keep the machines separate. During this earlier experimental time I discovered the tool Synergy which lets your mouse cursor travel freely (and drag files!) between desktops on different computers/OSes and that solved many of my problems.