If you would like to be around your family, maybe there's a shortline in your area that does local trips 5-6 days a week. That's what my local shortline does and that's why I plan to work for them once I'm old enough. All they require is the state's driver's license and a high school diploma and they will train you once you're hired. Agreed on safety requirements, etc. You could purchase a scanner and get the RR frequency for your area and hear what they do a lot of times. At each switch, when it is thrown, they always have to "double check" that it is definitely back to the normal position before moving on. Like Denzel Washington said to Chris Pine in Unstoppable,"In training they just grade you an 'F,' out here you get killed."
I'm kind of hoping that Trainz will further me ahead in the knowledge of running a train. But, of course, there is NOTHING like the real thing.
Is there is a Railroad historical society or something in your area that you can volunteer for? that's always a great start. I just joined one a month ago (
http://bellefontetrain.org/) and on their excursions you get to talk to the train crew (conductors, engineers, flagmen, etc.) and be a car host and ride along for free - just so long as you monitor activity in the car and help people on and off. You also get to punch tickets which takes about 10 min to go down one side of the car. You can talk to other car hosts and ask them all sorts of RR stuff.
When they don't have excursions, you can help maintain their track and practically work on the railroad. It may or may not be the same case in your area, but it's certainly worth a shot even if you have to pay for membership. Hope this helps.
Conducorboy