Shane,
You asked a big one...
If I were you and had hopes of getting a job on the Loop during the Summer or at the end of High School, I would start now.
A friend of mine and I began volunteering at the Colorado Railroad Museum before we were even old enough to drive. Go down there and ask Chuck Albi about it. It will get your feet wet, you can try different jobs and see which one that you like the most.
Since you want to get a job at the Loop, then I am assuming that you live in Colorado.
Maybe your dreams of being an Engineer will dissipate when you find out that to move over to that side of the cab you have to be a Fireman first. Firing is a dirty, hot job and on a short line or tourist line you are asked to do things that would never be asked of you had you hired out on a large railroad. You may not like sitting in a Sauna in the hot sun day in and day out.
You may prefer train service and meeting the riding public. But if repetitive questions get to you, you may prefer working on the track and building your physique.
Maybe sore muscles aren't your forte' and you would like to work in the shop on the locomotives or the cars. If you can't tell one of a wrench from another or don't like to have your eyes sunburned from a torch or welder, then you may find that your best job on the Railroad will be taking photos trackside.
But a museum is your best bet. Since your are volunteering your time, there are not many child labor or under 18 laws that apply. The museum will be greatful for your labor and you will learn to take direction as to how to do the work and complete it in a timely manner.
I started at the CRRM in 1967 and went to work for the Colorado Central Narrow Gauge Railway in 1970. This was the predecessor to the Loop, as the same operator ran both for a short time. I put myself through College during this period and thought that I wanted a job in business... Until I got one.
In 1975 Roy Breffle tracked me down and came to see me where I was working and personally asked me to come and fire for him. I thought about it and realized that I had never really been happy doing anything but Railroading. I handed in my notice the next day and went to work on the Loop the following week. I can truthfully say that I have never regretted my decision, even though the Railroad life is VERY difficult.
I am on call 24 hours a day, 7 days a week. I have worked every holiday on the calendar at least once and usually more and missed innumerable birthdays and anniversaries. It is Hell on a family.
But this is what I like doing, going to work is still fun and I, personally, wouldn't trade it.
Oh yes, the guy that I started volunteering at the Museum with? He's a Conductor on the BNSF.
Rick Steele