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I find that Emerson would be thoroughly disappointed with modern society. In fact, for Emerson, our reliance on technology would seem like a failure on our part as it is a waste of our human potential. For Emerson, individuals should only be relying on our own thoughts and ideas and all our knowledge should be gained by us going out into the world and learning about it by ourselves. Thus, to answer one of your questions, Emerson would most likely disapprove of us booking a "Genius Bar appointment" by relying on others and in the first place, would disapprove of the very notion of getting help from another individual. However, despite Emerson being correct that our reliance on technology has made us lose valuable skills, I wonder if Emerson ever considered how technology also helps us gain other important skills. For example, if you ever need to fix a broken sink then instead of calling someone to come and fix it, you can now google it and do it by yourself. Although, at the end of the day, humans do rely on technology more than they should Emerson's belief that one should only trust one's thoughts is not right either (i.e. consider the fact that that kind of thinking implies serial killers and psychopaths are right in their thinking).

Just to add to what AmericasObserver has said, I also doubt Emerson would view today's technology favorably. In the fourth section of Self-Reliance Emerson writes, "Society never advances. It recedes as fast on one side as it gains on the other", and suggests the invention of the coach - either symbolically or physically - has crippled humanity. His subsequent arguments against efficient transportation and the reliability of timepieces imply he had nothing but contempt for anything that made life easier.
Although I agree with the point about the ways in which the internet helps us exercise our independence, I'm sure Waldo would disagree. Despite the benefits of such a great tool, having all of this information readily available whenever we want it does seem to create a sense of dependence - we trust that the internet will always have the answer. In terms of "just googling it", Emerson has this to say: "A Greenwich nautical almanac he has, and so being sure of the information when he wants it, the man in the street does not know a star in the sky. The solstice he does not observe; the equinox he knows as little; and the whole bright calendar of the year is without a dial in his mind. His notebooks impair his memory: his libraries overload his wit". This sounds similar to learned helplessness but in a much more literal sense. Was Emerson the first to suggest this? Would we ever have to learn anything if we had all of the answers we would ever need just a few seconds away? I suppose Emerson's point is this: what would you do if your search for "how to fix a sink" returned nothing? He probably thinks your next search would be for local plumbers.