I had the same feeling about the evolution of the magsafe connector. The second generation, for which the cable ran parallel to the edge of the laptop where you plugged it in, was an upgrade in every way over its predecessor. The way it was constructed, and the forces you would typically put on it from day to day use made it much more robust than the T-shaped design.

But despite the obvious advantages, the next generation went back to the old design, but a little bit smaller, and back to all the old issues. I probably spent a few hundred dollars on replacement 3rd gen chargers alone, while the 2nd gen charger which came with my laptop is still in perfect working order in a box in my closet.

The cynical of me honestly wonders if they didn't see a decrease in peripheral revenue after the first iteration, and reverted to the old design only because of that.