Retired teacher, did the 30-day NARPass, in April, 2002 from Toronto at age 59. I have a detailed, notated itinerary which may be of interest to you, but of course, it tilts to my interests in American history, architecture and barbeque.
The route I followed included at least one overnight in: Chicago, Memphis, New Orleans, San Antonio, Austin, Fort Worth, St. Louis, Kansas City, Flagstaff and Grand Canyon, Los Angeles, St. Louis Obispo, (Car rental to San Francisco along coast highway), Monterey, San Francisco, Denver, Chicago.
I stayed mainly in 'Hostelling International' facilities, which provide clean and safe, low-cost accommodations to foreign travelers- young and not so young. The facility in Downtown Chicago (www.hichicago.org) is very hotel-like and is within walking distance of the world famous Chicago Art Institute as well as $200/night hotels. Occasional hotel treats along the way were because of low prices and/or proximity to rail stations.
I wouldn't do 30 days again, but on the other hand, the experience was unforgettable. I never upgraded to sleeper because I seldom had to spend more than one night on the train.
The meals in the dining cars were all first class and you get to meet a wide variety of people and exchange travel stories.
A final tip: Never sit in coach within 30 feet of a child under 5 years of age.
Dan A