Hey, Doyd, AllenTGamer just did a great review of his recent Amtrak trip with pics and everything. Check it out here:

http://neurotalk.psychcentral.com/thread49276.html

I've taken several train trips for entertainment, not so much for the travel itself. I love the murder mystery ones, and the dinner trains that run through major cities because you get to see "the rest" of the city, the back sides— the graffiti is excellent art!

I think you have the right idea, start more locally and see if you actually like travel by train. I tend to prefer driving over flying, train, or cruises because when I see something I want to look at, I can just go on my own schedule. The other modes force me to watch things as I pass them and wish I could stop to look, it's kind of frustrating.

Definitely take at least one or two shorter trips, everyone should go by train at least once!