One of the biggest issues that Apple has faced since Jobs passed away is brand dilution. Before his death, it was pretty easy to pick out a Mac or iPhone from far away, as they were tech staples in popular culture.
Unfortunately, beginning with the iPhone 5c, Apple tried to get too fancy. I thought the 5c could have been a throwback to the 1998 iMac, but they kept up with increasing options, which is arguably the opposite of what made Apple appealing. Too many choices is a bad thing for the common consumer, especially one that got used to Apple's standard black/white color choices, save a few generations of the iPod nano.
Now there's, what, 38 options? Too much brand dilution. I don't know if I'd recognize an Apple Watch the same way I recognized the first iPhone, iPad, or iMac.
Watches seemed like the next logical step, but they did it poorly. Too many choices too late hurt this release.