I'm a former seasonal employee of the Valley Railroad. It was a great job at the time. I was never a railfan, and have moved out of the area, so I haven't stayed current on operations at all. It's interesting to see in this thread what has been happening.
Here are some thoughts I had from my time spent working at the VRR:
1) There are some amazingly dedicated people. More so than anywhere else I have worked. Scores of people have worked at the VRR for low pay or no pay. They do this because they love the history and the equipment. The VRR is very lucky to have those people. When I was there I don't think that those people were recognized enough. Hopefully that has changed. (For the record, I don't consider myself one of those people. For me it was a fun job, but not a passion. I was feel that I was treated fairly.)
2) I was shocked to see that the VRR applied for a TIGER grant. It's not easy for me to say this, especially in light of the passion that people have for the VRR, but the VRR is not a transportation "business". It is a tourist railroad. I have always felt that the VRR lacked "business" leadership. Management has been hired to promote tourism. They have not been hired because they have expertise in developing a transportation business. This is not necessarily a bad thing - tourism is what pays the bills. However, I think the VRR needs to admit what they are, and what their management is best at. If they want to expand into more traditional operations, they need new vision. I recall when they were involved in the short line freight business in Middletown. IIRC, it was not a very successful experiment. If I were the federal employee looking at the VRR's TIGER application, knowing what I know about the VRR, I would have laughed. You can fix the track all you want. Until you get experienced management installed, it is never going to be a viable freight operation. While I don't enjoy saying this, the VRR was the most poorly run operation from a business perspective that I have seen in my professional career.
3) Luck plays too much of a role at the VRR for engine crew promotions. If there was no need for engineers, you would be stuck as a fireman for years and years. But if you were in the right place at the right time, you could be promoted very quickly. This was very rare, but when it happened I felt badly for the people that had put in so many years to get to the same place.
4) I think the train crews need to be reorganized. I think you should have on every crew: a) a person who focuses on operations; b) a person who has knowledge of history; and c) a person who is focused on customer service from a tourism perspective. The VRR is a tourist attraction that is a railroad. Having a train crew comprised solely of railfans is not a good idea. In my experience, many of those individuals did not have a good sense of public relations. It certainly wasn't their primary interest.
5) I've always felt that the grounds needed to be spruced up. When I was there, everything was just so darned dusty from the parking lot. I haven't been there for quite some time, but it seems that this has not changed substantially. When I worked there, there was very little to separate tourists from some dangerous areas. I think it's great that tourists can see work being done on antique equipment. That should not change. Nonetheless, there needs to be some planning on safety and there also needs to be some recognition that certain areas need to look nicer and certain things should be kept away from the public.
6) The VRR has gotten much better at marketing since I was there. The special events have maximized revenue - especially during some otherwise slow times of the year.