FastTrack reduces the webmaster's load by letting multiple publishers manage their own files. It works the same on Windows 95 and NT systems, so upgrading is easy. O'Reilly's WebSite Pro is loaded with features, thanks to bundled third-party packages. It is relatively straightforward to administer on Windows 95 and NT via its Control Panel. However, for remote administration you must have a copy on the local system as well as the remote one, which raises the software cost significantly.
Documentation is excellent, with many screen shots, examples and explanations in the three manuals.
NT-friendly Microsoft's Internet Information Server has features similar to those of FastTrack and WebSite Pro. Unlike them, it is tightly integrated with NT and relies on NT's user and group databases for access control. It can be managed remotely. For Windows 95, my choice is FastTrack. For NT, it's hard to top Internet Information Server, which comes free with the operating system and full of features.