It didn't actually work that well. The internet is the only real way you can get a Google-maps like autoroute feature with reasonable update times. Constantly buying new CDs and DVDs on a subscription basis is a no-go for sure. I don't think anyone's 56kb modem was fast enough to update the map data.
Even if you bought the CDs for the updated map data, it only was updated every year IIRC. So there was plenty of roads that simply were wrong. Its been a long time since I used it, but Google Maps is better at the actual core feature: having up to date maps, and an up-to-date route information.
Hint: Microsoft wasn't sending around Google cars to build up its database of maps in the 90s. Nor were there public satellite images released by the government to serve as a starting point for map data. (Satellite imagery was pure spycraft. We knew governments could do it, but normal people did NOT have access to that data yet). The maps were simply not as accurate as what we have today, not by a long shot.
--------
Has anyone here criticizing new software actually live in the 90s? Like, there's a reason that typical people didn't use Microsoft Autoroute and other map programs. Not only was it super expensive, it required some computer know-how that wasn't really common yet. And even when you got everything lined up just right, it still had warts.
The only thing from the 90s that was unambiguously better than today's stuff was like... Microsoft Encarta, Chips Challenge and Space Cadet Pinball. Almost everything else is better today.