On its current path, I feel that Android is destined to the same fate. Android is just as open as classic Windows Mobile, allowing OEMs to completely change the interface, build a massive variety of form factors, and come up with hardware variations that often lead to underpowered devices. The only real unifying aspect between Android devices is the Market.
Examples? Recently I used the Motorola Backflip, a device crippled in several ways. First, the MotoBlur interface, while sort of cool for teenagers, was confusing, not elegant, and very slow in terms of performance (or perhaps the device was just underpowered/not optimized to begin with). Second, the hardware (with the backflipping keyboard) will be seen as a novelty to most people. And third, the device was crippled by AT&T by coming with last year's version of Android and the inability to install non-Marketplace apps.
Case two: the Sony Ericsson XPERIA X10. While a powerful device under the hood, the Rachael interface that probably cost SE tons of money and time to develop is slow, confusing, and difficult to use. As shown in recent a Engadget review, the device often goes from being snappy to slow without any given reason. Back at CES I had a chance to use the X10, and while I was wowed by the eye candy, I knew I'd have a hard time living with the device as a daily driver.
And yes, there are some great Android phones out there like the Nexus One, Hero, and soon the Legend and Desire. What do these devices have in common? They're made by HTC. If you think back to Windows Mobile, there also have been some really good devices over the years like the Touch Diamond, Touch HD, Touch Pro2, and HD2. And yes, these devices were made by HTC as well. If HTC was the only OEM on the planet, perhaps legacy Windows Mobile and Android of today wouldn't have these issues, but that's just not the case. If 50% of device on a given platform are crappy, it can overshow the other 50% that are good.
The smartphone industry is in its relative infancy. We're starting to see what works and what doesn't from a user experience perspective. Apple thinks that the best user experience comes only when one company controls the hardware and software experience. Microsoft thought the complete opposite for a decade with Windows Mobile...that the best user experience comes when they have a plethora of choices, and when OEMs can be free to do whatever they want to the software and hardware. Microsoft has gotten smarter, and while Windows Phone 7 Series will be perhaps a bit *too* much locked down, it's a step in the right direction that will ensure that if and when you buy a Windows Phone 7 Series device, it won't suck.
But for Android, there will be some struggles ahead unless Google and the Open Handset Alliance can figure out a way to put a tighter grip on what the OEMs and carriers can and cannot do.