Question:
Is there a way to tell if a USB device was plugged into a device around a specific date range while also displaying the drive letter that would have been associated?
Answer:
It isn't something that would be visible through inventory, but if "Device Manager" or "Shadow Copy" is enabled there would be potential to see something.
In the case of device manager you would have to know the device id of the associated device in order to see any associated information.
In the case of shadow copy it would leave a trail on the hard drive of what would have been copied over.
But in both cases there wouldn't be an indicator of the drive letter associated with the USB device used.