Here is my feelings and thoughts, coming from a rookie railfan, as well as an aspiring radio personality:
-There are some jobs I classify as "Dream Jobs" or "Ultimate Jobs". These are the occupations that are a little unusual, and specialized, that people grow up wanting to be (Doctors, lawyers, radio personalities, rail workers, et al). These careers are so specialized that it's hard to get an idea of what it would be like to do it unless you ask someone who's been around for a while. In these cases, asking a question like "What is the average salary/job environment/benefits?" is perfectly fine.
-I find it amazing, and shocking, that there are engineers who feel that being a railfan makes you somehow less qualified. I'm guessing that railroaders got into railroading because, at one time, they liked the railroads. True, some railfans can be annoying, but most of the ones I've read about are unobtrusive.
-Fianlly, my personal belief is that when you get into a line of work that you grew up wanting to be in, it does not mean you have to give up being a fan. That is true in any "Dream Job".