Yeah that last descent into Port Jervis is nice. Good views and a nice curvy drop all the way down into town. There are a couple of pics of the roebling bridge on that last link in the original post.
No problem at all with the trains. Unloaded the bikes and stood them up and carried them up the stairs one at a time one hand on the stem and one hand on the down tube. The conductor was very accommodating and even helped us get our stuff off at our stop. New Jersey Transit has become much more bike friendly in the last year or so although they still have peak time restrictions.
Yes below Dundee on the western side of route 14 and into Watkins Glen is beautiful. The sun was out up on the ridge and there were severe thunderstorms passing through the valley right over Watkins Glen and the Lake. Quite a sight and when we hiked into the glen the canyon was overflowing with water. A nice show all around.
We rode up the hill and camped in the state park campground. It was very nice, clean and quiet with showers and rest rooms and there was hiking access to the glen from there.