Nice ride! I'm jealous. Always wanted to do that, but the traffic in spots is insane. And, yes, the stretch of 109 leading south towards Wolfeboro is in deplorable condition, and has been since last fall. I'll bet they are waiting until the "season" ends before giving it a proper resurfacing.
Re: Hills -- My local favorite is the long hill heading out of Melvin Village before you get to the view at the Wawbeek road. When I run that hill, I make sure not to look up.