I think the lessons are clear, though—
1) People can have both good and bad ideas (Chrysler Limousine vs convertible, Chrysler 200 vs crossover onslaught)
2) When The People decide the form of a car is out of fashion, it’s gonna be really hard to sell.
There's a lot of timing involved. Today, it would be foolhardy to launch a really competitive compact car like the 1995 Neon or 1981 Reliant, because people just don't want them; but a compact crossover would be smart, even if it's not top of class. Back when the Caliber was launched, the opposite was still true. The same car in “crossover” and sedan form was available from Toyota and Chevrolet, and it sold like hotcakes as a sedan, and kinda poorly in crossover trim. Caliber was doomed by its form factor just as Chrysler 200 was.
Not renaming the Chrysler 200 when they launched the new one was, IMHO, a major error. I would have either gone back to Sebring and highlighted the improvements, or chosen a classic name such as Newport. That said, the rear seat access wasn't as big a problem as getting anyone to consider a Chrysler 200 at all, especially when people had a choice of Camry and Accord (or Mazda5 for those who want to be different) anyway. Consumer Reports was not going to recommend a Chrysler when you could have a Toyota or Honda... I fear that's part of the Malibu and Fusion issue, too.
Old Chrysler management tried to match the most popular cars of the day, one to one, and failed dismally. When they struck off on their own, they succeeded wildly. I think SM or his minions might have had some chats with museum curators...
History also teaches us that it doesn't matter if you make the highest performance car, as long as most people think you do...