Sure, Sony's backwards approach meant that companies like SanDisk were able to get ahead of them, but their devices just don't have the interface that Apple's iPod has. And Sony has been really old-fashioned in their approach to their devices recently. Where Apple has used new technology to create better interfaces, Sony just hasn't kept up.
The issue today is that no one (except possibly Palm with its soon to be released webOS) has been able to match Apple's interfaces, never mind exceed them. And with Apple's volume, it's hard for a competitor with a poor interface to undercut Apple on price. So you get items like the Dell DJ which costs the same, but isn't as well designed.
For Sony to regain its position in portable electronics, it really needs to figure out the interface that will make people's lives better than Apple's (or at least just as good). Palm might be doing that by equaling Apple's touchscreen design and going a little further with its "cards" metaphor, but that's a bit of hopeful thinking on my part (as much as I like Apple, I like competitive markets even better).