I'm pretty sure the majority of people don't even know what "Ice Cream Sandwich" is or what "Jelly Bean" is, and go about perfectly fine and happy with whatever OS version their phones are on.
Having said that, I'm all for less carrier interference and better support from companies, so fragmentation is a problem, but it's one that is overblown. The whole idea of Android is to be on as many platforms as possible (it's working too). Fragmentation is inevitable when an OS is meant for as many tiered devices as possible with varying degrees of support.
So yes, it's very possible to pick a really terrible and/or poorly supported Android device. This is where research goes a long way because it's also possible to pick a great Android device. If updates are that important to you, the Nexus line is the way to go, despite some growing pains and missteps (I criticized Google for allowing the Verizon Galaxy Nexus debacle to happen; that was a real foul up). The Nexus line are the best guarantee of updates, and now that the Google Play store has come to its own, I foresee the Nexus launches to be better.
It's really not that difficult to understand Android. It's just the nature of the beast, and intentionally so. Those who don't understand Android's model, or dislike it because it's different from Apple's will continue to obfuscate what it's about and use "fragmentation" as a talking point against Android when it has so little to do with the actual experience of the OS itself.
Meanwhile, ICS/JB continue to propel Android ahead at a far greater pace than iOS is moving.