I thought Sony had learned their lesson after losing completely and utterly to VHS. Most would agree Betamax was a superior product, technically speaking, but being the 'better' product is no guarantee of success - pricing and marketing are critical. They priced themselves out of existence.
Blu-ray was a much better roll-out. They enlisted major studios before the product hit the market. Licensed it to many other companies. And the pricing - while still not making most happy - is keeping them in the game. (And Toshiba's HD DVD died just like Betamax did before it)
I had a pair of the Sony eReaders. They were great - insane battery life, excellent controls. And no stupid touch-screen - like any sane person wants fingerprints on their reading surface? OTOH, the software, as you said, sucked big-time. And then, both readers died within a few months of each other. And my customer experience with Sony pretty much drove me to the competition. And while that is a technically inferior model, I don't suffer from the software pains that Sony caused.
My Sony library still exists - inaccessible - on my hard-drive, thanks to their !@#$ DRM insanity. Again, part of the friendly service from the Sony people - their advice began and ended with 'Buy a newer Sony eReader!'