I certainly don't see any such issues using LPC-Link2 on a Catalina-based Mac here (though that machine has no VM software installed). Nor do I see such problems on my own Mojave-based Mac when running Parallels VM.
To be honest, the usual problem when using VMs is when trying to debug from the VM itself rather than the host machine. In such circumstances, we have occasionally seen issues where the VM fails to spot the USB device reenumerating after the probe firmware is softloaded - which can typically be solved by detaching / reattaching the USB device within the VM software's menu system.
I can only assume that in your case, your Fusion setup has been configured such that it always grabs the LPC-Link2 device as soon as it enumerates?
Anyway, glad to hear that programming the probe firmware into the LPC-Link2 using LPCScrypt has provided a way forward for you.
Regards,
MCUXpresso IDE Support