Circa 1993, my family was using (Autoroute?) a DOS based driving directions program. I believe this is what ended up evolving in to MS Streets & Trips. Anyway, it was pretty good. It was geared towards a user that is trying plan a trip with features to match. You could specify that you wanted to stay off certain types of roads, you could mark certain points you wanted to stop along the way, specify how fast you drive. It would give you choices like a) fastest route b) shortest route c) scenic route.
I wanted to point fellow ski house mates to the best way to get to Mt Snow VT and just tried to get one the heavily touted and heavily invested online services to do something even close and came up way short. They insisted on I-95 and anyone knows that has actually done the trip both ways, you want to take the Merritt parkway. I guess I’m just pointing out that I might prefer to have a few more practical features pushed up the priority list before some of the more eye-popping stuff. Granted the new MS Live bird’s eye view is incredible.