Way back when Apple first put out the iPod Touch, I thought it was a great idea. The thing is practically a computer! It fits in my pocket! I looked at the iPhone as being a waste out the gate because really, AT&T? Might as well chuck myself off a bridge.
Years later, I've found myself in an annoying conundrum. Every major OS revision that comes out costs a fairly small fee, $10. Certainly not terrible. I paid to upgrade to 2.0, but now we're at 3.0, and looking at the feature set, I think, meh. Nothing I really care about--sure, copy and paste are great for text apps, but I rarely use my iPod for text anything. Music, games, web browsing. So I chose not to pay their fee.
But now my apps demand I upgrade. I foolishly allowed them to update themselves, and they promptly broke because they all require I have OS 3.0, minimum. I'm not sure if it's a contractual requirement of building apps for the platform, but none of the apps I've seen still support OS 2.x. So my device is now shackled to the basic functionality supported, which is nice, but I can't get any apps for it without jailbreaking it. Apple is attempting to extort me to get the functionality advertised. Seems like fraud to me.
In the words of an iPhone dev I know, "anyone not willing to upgrade their OS is also not likely to pay for apps so, fuck you." Thanks, Apple, for letting your representative tell me how you really feel.