If you look at the image above, you'll see one of my cities and two outposts.  The second outpost is in the bottom left with an army camped on it.  Now notice the roads. They go from the city to each outpost, but not between the two outposts.  Off to the right of this picture is a considerable part of my kingdom, so units would likely traverse a path from the bottom left outpost towards the right outpost and on further right.  

I have Economics obviously.  Looking at future techs, I assume that there are no other road enhancing technologies so I will never have a road that connects those two outposts even though such a road is strategically significant to my kingdom.  

The automated road system can work, but it needs to be more intelligent about where roads end up.  If I had a Civ-like ability to build my own roads there would absolutely be a road linking those two outposts.  My military production is all off to the right and my next big war is down and to the left.  

In order for the automated system to be satisfactory roads should have developed between those two outposts.