Your request raises an interesting issue. A great deal of philosophy, east and west, has some of what may be called religious inclinations, as does philosophy out of Africa (pre and post-colonial) and the Americas. But that should not deter you if you are uninterested in such an inclination, as the philosophy that has been generated from Hindu, Buddhist and other traditions in India and China (and elsewhere) contain a massive amount of philosophical arguments that can be engaged from a secular perspective. There are multiple Buddhist arguments about the nature of identity, for example, to delight a secular philosopher who is interested in metaphysics. And Moism in China can provide a good focus if your interest is in ethics and utilitarianism. In terms of access to philosophy from around the globe, I recommend the Blackwell Companion dedicated to world philosophy.
Hm, are you asking an ethical question here? (ie it might be wrong to use your 'connections' to get into a 'better' school than you 'deserve'? I put all that in scare quotes because I think a lot of work would have to go into posing that question clearly, as an ethical question.) Or are you really asking the more practical question, "what would be best for me overall"? Re: the latter, I'd say get into the "best" school you can legitimately (ie ethically) get into -- for being surrounded by very bright people, not only faculty but especially your peers, would stretch you as far as you are capable of being stretched ... Of course you can get an excellent education in lots of different places, esp. if you are motivated and dedicated and go out to acquire it yourself -- but unless you are the type to be cowed by very accomplished peers, to feel diminished by them, then you ought to surround yourself with the best you can in order to become the best you can ....
Great question! By the way you pose the question (Thales to Rorty) I assume you mean western philosophy. Yes, I think you can carry out such a project, reading a bit of each of the major philosophers and then relying on a good history as a guide. I would highly recommend Anthony Kenny's multi-volume Oxford University Press books as lively and engaging. Copleston's history of philosophy is perhaps less engaging but it is reliable and a good companion. Speaking of Companions, Blackwell, Oxford, Cambridge, and Routledge each have massive Companion series that would also be helpful in filling out your reading. You might want to set as a goal an overall grasp of the history of philosophy and then dig in to a few areas and thinkers so as to deepen your understanding of philosophy and also to engage more in the practice of philosophy (wrestling with arguments and counter-arguments) in reference to a specific area or philosopher.
Probably Karl Popper's work comes the closest. Get his book (I believe in two volumes) on the enemies of a free society. His work was taken seriously by eastern Europeans who were under the authority of the Soviet Union. Popper provided them with an alternative perspective by which to offer a critique of communism. Popper's work is systematic and fair (except in the case of his critique of Plato, which I believe to be based on a partial misreading of Plato) and historical. A book that is less historical but is profoundly anti-collectivism (and thus communism) is Robert Nozick's Anarchy, State, and Utopia. The latter is full of great arguments, colorful examples, and well worth a slow read.
It is rather difficult to believe that you have correctly describe your assigned task -- is it really to write at length about the notion of being in the Sophist without consulting any commentaries or interpretative essays? Well, not to beat about the bush, that project strikes me as simply ludicrous. You need all the help you can get if you are to work your way into a text some two and half thousand years old (in fact, I take it you are relying on a translation which has already made some interpretative moves that themselves raise issues): it is just absurd to pretend otherwise. Unless, I suppose, the point is to reveal to you the impossibility of the enterprise and make you appreciate that relative beginners need the commentators and the philosophical interpreters -- but then that is a pretty dumb way of getting you to see what is already an obvious truth.
I don't have too much of my own to add (but see below).
Really, I wanted to recommend to you the work of philosopher Neil Postman. He was the go-to philosopher on the issue of technology and citizenry. You might want to start by looking up his lecture called "Five Things We Need to Know about Technological Change." Currently there is a link to it here: http://www.mat.upm.es/~jcm/neil-postman--five-things.html - not sure how stable that link is. You can also find out more about Postman and his books at http://neilpostman.org/ -- but I am not sure who owns that website. Good luck, I think you will enjoy Postman.
P.S. I agree that philosophy generally has been cautious about technology. But perhaps contemporary philosophers have special reason to be cautious: philosophical enterprises that make use of technology quickly break out to become their own (better funded) fields - as in the case of psychology, physics, cognitive science, etcetera.
P.P.S As to the issue of philosophy students today, I can only speak from my own observations. Students' attention spans are getting shorter, but their ability to conceptualize complex problems with original visuals or graphics is impressive. These trends do impact how I teach. I won't repeat the experimental course where I only assigned one book (Plato's Republic) for fifteen weeks. On the plus side, my classes now feature plenty of chances for students to draw or doodle concepts to make them their own. A good day is getting thirty 'updated' drawings and essays on Plato's cave -- where students are self-aware enough to depict themselves as being prisoners chained to the cave wall of the internet!
Strong performance in a rigorous college-level philosophy class is a good positive indicator of philosophical talent, but poor grades, whether in college or in high school, cannot generally be taken as evidence that a person lacks philosophical talent. The reason is that there are just way too many reasons why a student might do poorly in the classroom that have nothing to do with philosophical ability. I know of at least a couple prominent philosophers who were indifferent -- or, in one case, lousy -- students until they discovered philosophy, and were really grabbed by it. Some students are handicapped by depression, stress, or other personal difficulties, and do not do their best work. Many students are just not that into school, or don't care about grades.
Another thing that makes it difficult to predict who will make a good philosopher is that there are lots of different ways one can be a good philosopher. I spoke above of "philosophical talent," but there's really no particular way to do philosophy well. There are some necessary conditions: you must be able to think clearly and logically (but most people can do that if they are sufficiently motivated to do so), and you must have a taste for abstraction. Beyond that, though, there are lots of different kinds of mental talents that can compose an excellent philosopher. Some philosophers have excellent memories, some are adept at thinking up illuminating examples, some are good at synthesizing ideas from different domains, some seem possessed of sound "hunches," some have a facility with formal methods. But for every one of these "sub-talents," I could probably name a prominent philosopher who lacks it.
Some people -- administrators of liberal arts colleges, for example -- will insist that there is some general mental ability -- "critical thinking" or "general intelligence" -- that is implicated in all academic work. But others, like psychologists Stephen Ceci and Richard Nisbett, think that "intelligence" is domain-specific -- that is, you can do very well in one subject and very poorly in another, or you can do well in "applied" contexts, but poorly in the classroom. Factors like your level of interest and your level of effort turn out to be very important in explaining academic success.
In sum -- the only way to see if you're any good at philosophy is to give it a try. But be prepared to try hard.
Another alternative is to read Kant's very own "Cliff's Notes" version of the Critique, namely, his Prolegomena to Any Future Metaphysics. Again, there are numerous inexpensive editions, or go to your local library; it's also online at http://www.mnstate.edu/gracyk/courses/phil%20306/kant_materials/prolegomena1.htm (and probably elsewhere). It's much shorter than the Critique, and much more readable. And well worth reading!
Ethics is not about teaching people about how to be good, so we should not be surprised that those both studying and teaching the subject are no better, and hopefully no worse, than anyone else. It is well known that librarians often complain to the philosophy faculty that books on ethics are the ones most stolen from the university library, as though they are also surprised, but we do know that people often teach and study a subject without being well organized enough to apply it to their own lives, or even see the need to do so. Students who cheat need to be punished whatever their subject of study, and the only difference here between a student of ethics and one of engineering is that the former might be expected to know something of the different theories that lie behind punishment, together with the nature of moral rules, whereas the latter might not.
Should we be surprised if a mathematician gives us the wrong change? Can a child psychologist produce dysfunctional offspring? Do home economists sometimes burn the pudding? Similarly, ethicists sometimes err morally and we should not regard this as a special sort of problem at all.
Many people do find philosophy quite difficult, but most people find that doing philosophy at least at some level is profoundly natural and fundamentally human. Aristotle said "philosophy begins in wonder." I think that's right. So my advice to you would be to allow your "wonder" not to be stunted by the artificial limitations of worries about grades. If you do start doing badly, have a chat with the teacher to see what you can do to improve. But here is something you probably already know: You do better at things when you find a way to enjoy them. This can be hard, yes; but it can also be great fun and very interesting...actually wonderful. So try to enjoy it, rather than fretting about grades!