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Buying an Apple device and getting "updated" is no better. Even though you are "updated" to the latest version, they leave out features or cripple them compared to the newest iDevice. Apple lacking fragmentation is a flawed perspective many succumb to (not saying you are one of them) and is another way they manipulate users into thinking they have the latest OS. At least when Android's get updated they get ALL the features. The reason why updates are delayed is for 2 reasons (which I'm sure you're aware because I know you're a knowledgable guy):
I agree that updates are a bit of a gamble, which is why I own a Nexus. I wish Google or the manufacturer came out with a list of "what this device will support" but since they don't it is what it is. The thing is, the hardware is moving at such a quick pace that it is ahead of the software. With the need for so many choices within Android, it's hard for Manufacturers to stay content with 2 models of phones, Moto fans know how much this hurts. However that doesn't mean ONE device is the answer either, look at syndicate's example.
I went with Android originally because of the support the dev community showed. It was pretty nice before Android got big with the OG Droid, but right after the OG Droid came out it was almost like the ".com boom" of the dev world. Support was absolutely insane for Android and things have only gotten better since. However, to stay up to date on Android versions today is to either rely on the dev community or to buy a new phone at what seems every other month.