I have solved the issue. It appears to be the fault of a bug in Windows XP. If you navigate to the registry key:
HKEY_LOCAL_MACHINE\SOFTWARE\Microsoft\Windows NT\CurrentVersion\Drivers32
Then go to the "midi1-9" keys, you will see that most are probably taken up all by the same driver. Delete one and reinstall the Roland usb midi device driver, and all works well. Apparently there is a 10 driver limit, and windows once hitting that cap will not install anymore drivers, even if all 10 drivers listed are the same driver.