i'll be following this one closely for my own education. i don't really have specific answers for you, since gps didn't exist last time i rode amtrak.
i have an Etrex Legend, which i have been quite happy with. it has been failing lately, so i just bought a compact flash type gps receiver that fits into my Dell Axim pda. this gives me a larger screen, with color, and the software even gives me voice directions while driving. it's the Globalsat bc-337, and i'm using software called Pocketmap Navigator.
the etrex legend is small, and doesn't have color. the one good feature is that it runs on 2 AA batteries. my new gps/pda combo will have to be recharged on the train every few hours. the one big advantage my new setup has is that it has an external antennae i can plug in, and stick to the train window with the suction cup. the legend would have to be held up to the window constantly.
there are also inexpensive gps units that hook up to a laptop via usb. these are not very practical when driving. some of these can also be used with a pda if you have that. if this interests you, search amazon.com for microsoft streets and trips 2006. they were selling it with the gps device included for only $65 earlier this week.
i may be able to give more advice, depending on the main uses your son will have, and your budget.
i'll give a report on how well my setup worked after my january trip Chi to Reno.