The virtualisation problem may definitely play a role! In my experience, ClearType in a VM is often very very wrong. I think it may even be off by default if Windows can't find details about the current screen.
Alternatively, you may be getting the "RDP" experience for optimized drivers, which is just very blocky.
I prefer ClearType over whatever macOS does (or did, been a while since I had a Hackintosh) but combining different rendering styles is always jarring. Helping Mac people through remote desktop always made the text look wrong to me, probably for the same reason. When you expect text to look a certain way, alternative renderers are always wrong.
This is also something I notice with some custom GUI libraries that implement their own font rendering. I've dropped several GUI tools because I just got frustrated by how their text always looked different from normal text.
The only time I had dislike for ClearType was when I'd rotate a monitor from landscape to portrait. This makes sense, since the subpixel layout is then wrong. So, I'd usually just redo the ClearType settings when rotated and use the monitor in that orientation for a while instead of constantly switching.