The 911 is timeless for a number of reasons: Porsche have spent years keeping the brand and style consistent. It was expensive and exclusive, which made it desirable.
But that care was very hard to drive. If you don't know what you're doing then you will not get anything like the true performance it can give.
It was also very expensive, so only those with the adequate resources could afford one. These were not always people who could get the true performance out of the car.
The Cad, on the other hand, is a fantastic car in its own right. Widely available, easy to get its maximum performance, perfect for almost any job. OK, so it doesn't look as sexy, and for seriously hardcore tasks it doesn't perform as well as the Porsche. But if I had to pick a car that was most likely to be reliable today then the Cad is an obvious choice.
Even more damning; Caddillac, like Porsche and the 911, were still making that brand of car up till ~2006. You wouldn't recognise it though because the shape and performance has evolved to meet modern needs.
It's sad to see his list of languages; whilst I would agree C is a ridiculously good language, smalltalk and lisp? They've always struck me as pretty specialist. Conversely a lot of production code still uses Cobol and Pascal. And what about Fortran? Or Delphi (wasn't Skype written in Delphi originally?).
I know we're hackers, and so it's hip to drive Prosche's. But it is sometimes sad to see how we forget about a massive section of our industry who also do cool things, but tend not to have blogs...