The category is "A Special Train Car"
Reminder....The answer is in the form of a question.
$400 - Dating from 1916, the Cannery Row one of these train-ending cars is an attraction in Monterey, California.
$800 - The rail car named Ferdinand Magellan carried FDR 50,000 miles in 2 years; his last journey was to this state in late March 1945.
$1200 - (Daily Double Question) An epically terrible trip from Buffalo to Westfield, N.Y. inspired this man to create the comfy rail cars named for him.
$1600 - (A photo is shown of a Grand Canyon car with windows wrapping across the entire 2nd level) These cars named for the architectural shape up top were the ultimate in mid-century luxury and great views.
$2000 - Sarasota's Circus Museum has the private luxury rail car of John from this fraternal family.