I think we also have suffered a bit from playing the Beginner's Box first, just in that they made characters for what we thought was going to be a one-shot trying out a different system, so nobody worried too much about character backgrounds or motivations - just finding a class that interested...
I think I haven't done a great job highlighting the NPCs in town. I wanted to avoid the info dump of "here are the 26 people whose names you need to know" and was introducing them gradually, but probably without enough of a hook to make them memorable. I wrote up a cheat sheet for the players...
You could look at "Troubles in Otari", which is a series of 3 adventures meant to be run right after the Beginner Box. The adventures are level 2, 3, and 4, and involve some wilderness travel.
I haven't played or run them (yet), but I did run the Beginner Box and we rolled right into...