Is the Best Fare the Best Deal?

A question came in by email the other day from a lady expressing irritation that Amtrak fares seem to change for no apparent reason. Welcome to the club, ma’am.
As it happens, I’ve been thinking about visiting my sister in Florida following NARP’s 50th anniversary celebration next November in Chicago. She lives in a little town a few miles from Orlando near DeLand, so the most direct route would be to take the Capitol Limited from Chicago to Washington, connecting there with one of the Florida trains.
Ah, but do I leave Chicago on Sunday, the last day of the NARP meetings, or stay an additional night and leave on Monday? Once I get to Washington, do I take the Silver Star or the Silver Meteor? Both stop in DeLand. And how will those choices affect the fare?

 First issue: the Capitol Limited (shown above near Harpers Ferry, WV) arrives in Washington at 1:05 p.m. and the Silver Star departs at 3:05—a two-hour connection, and that makes me nervous. The Silver Meteor leaves Washington at 7:25 in the evening, but that means sitting around Union Station for six-and-a-half hours.
But there’s something else to consider: the Silver Star doesn’t carry a dining car. Food service on that train is from a café car, is microwaved, and everyone—both coach and sleeping car passengers—must pay for their meals. The Silver Meteor does have a full-service dining car and meals on that train are included for sleeping car passengers.
Of course I want a roomette all the way from Chicago to DeLand, so now figuring the cost gets complicated because, understandably, a roomette on the Silver Meteor costs more than a roomette on the Star because dining car meals are included in the fare.
After an hour on the Amtrak web site, here are the alternatives: If I leave Chicago on Sunday night and connect with the Silver Star in Washington on Monday, my fare is $602. If I connect with the Silver Meteor later that same day, the fare will be $726.
But if I wait and leave Chicago on Monday and take the Silver Star, the fare is $482. If I take the Meteor, it’s $550. Wow! Stay an extra day in Chicago and save $120 if I book the Silver Star and $176 if I choose the Meteor. Of course, the extra night in a Chicago hotel will cancel out the savings . . . and then some.
And this is weird: the Meteor costs $124 more than the Silver Star on Monday, but only $68 more on Tuesday. And it’s the exact same menu on both days.
I really do feel sorry for someone new to all this.