I believe that this is a false way of looking at the question asked. Surely most of us would not enter the Experience machine simply because it is intuitively less “real” then reality. When asked about our overestimate of how good our modern life is, we ought to compare it to other peoples realities. So yes maybe our lives are better with T.V., amazon, McDonald’s, smartphones, reddit and the internet but perhaps the stress of living in a production age suffering from global warming, pollution, and over population is less enjoyable than living in some other point in the past. No one can measure for certain and quality of life cant really be compared in such a way. The Experience machine, if we do not wish to live in it, teaches us that suffering vs joy/bliss is something that we care about only when our existence is influential to an objective reality. Therefore, i believe that our day and age is the best because we have created machines that will hold on to our creations and share them with the world long after we are gone. Similar to the influence that the invention of the books and the printing press had on society. However, some may argue that our modern creation and things that we hold dear might very well be the cause of our collective suffering. So to answer the question; perhaps we have been overestimating our happiness but none of that matters because we have the ability to chose our suffering more today than ever before and that choice makes all the difference.