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One of the issues that can come up is that your W: drive is there, but may have a red X over the icon for the mapped drive. You can find this icon by browsing to my computer. It is possible that there is still a problem and the red X does not show.
If we browse to MyComputer and then double click on the W: drive it should show us the contents of the W: drive. At this point the red X will dissapear. Now try to re-open System 5 and you will be able to log in. If this does not work, please call Technical Support at Windward Software 1-800-663-5750.