What does it say about our society that some things that Orwell considered dystopian and a result of an authoritarian regime we choose to do of our own free will?
I think it says that Orwell was right. Simply put, Orwell understood that elements of the authoritarian structure that Big Brother and the Party demonstrate are aspects in any modern political system of control. It is naive to think that Orwell did not believe that the liberal democratic orders of America and England could not fall into some of the same habits of political control that Oceanic citizens endure. For example, I think that Orwell would shudder at the willingness to sacrifice so much of personal freedom and liberty. The usage of the web and cataloging of browsing habits is a form of technological control that Big Brother would have loved to employ. Enabling Cookies would drive Orwell crazy. There is very little outrage at such a condition. In the modern setting, we seem to take this violation of privacy as part of what it means to be "digital citizens." Orwell would be puzzled at the ease with which internet use and sacrificing privacy go together, and would simply be outraged that citizens willingly do this.
I tend to think that the same level of outrage would be displayed at how easily the sacrifice of political liberties happen in the modern setting. The "War on Terror" and its elusively perpetual nature are right out of the Party's playbook. Ensuring that citizens are constantly immersed in a condition of war helps to centralize political power and authority over the body politic. For Orwell, the lack of sustained outrage on a large level over this would be difficult to comprehend. We are at a point where our leaders openly say, "Personal freedoms need to be sacrificed to fight the war on terror" or that "Everyone spies on everyone else" to justify encroachment of individual rights. We simply accept these explanations without asking any large scale and mobilizing questions to change such a condition. Orwell would not understand how individuals in the modern setting could so easily embolden the political structure and authority in taking away the intrinsic nature of many individual rights.
Finally, I think that Orwell might have an interesting take given the condition of Edward Snowden, the so- called "NSA Leaker." I think that Orwell might see Snowden as a voice of dissent, seeking to fight the system. There are elements in Snowden's narrative that might paralell the personal rebellion of Winston. Both worked inside the system that they end up rebelling against and both are seen as intense threats to the authority structures. With this being the case, Orwell would not have difficulty understanding why so many nations are shying away from granting Snowden asylum. Political orders benefit in such alliances with one another and he would get that.
Where Orwell would have challenges would be in understanding how little public outrage there is. Snowden's condition in being grounded in the Moscow Airport's International Transit Lounge does not evoke outrage or public rallying. Orwell would not understand why there is not a larger sense of activism in helping Snowden. Rather, individuals simply see it as voyeuristic entertainment. It is drudgery as opposed to a political battle between authority and the individual. For Orwell, the condition of Snowden and lack of social outrage and mobilization represents how authority structures have won in being able to silence and mold the will of the body politic, something that Big Brother and the Party cling to as their basis for power in Oceania.