Only found out about the Wee Shu Min (think farmer vs scholar) saga today.
This "elitism" in Singapore is something I felt very strongly when I first migrated to Singapore from Hong Kong. I've always been good with exams so I know the system works in my favor. But I was very frustrated with the streaming system which, in my opinion, really affected my younger brother's potential (I shalln't go into the details, suffice to say that I'm not impressed with this arrangement at all). It always baffles me that streaming starts at such an early stage, and the mobility between the "top" and "lower" class is so low. Essentially, if you screw up early (in schools' exams), you don't really have a very high chance to recover later on.
However, I can't place the blame squarely on Singapore's streaming system. It is also this prevailing, overarching assumption in the society that success can only be obtained through better formal education. Compared that to Hong Kong, where there's also some form of streaming (though somewhat less rigid), the pressure is not so much for the kids to perform in schools. There're just so many counter-examples (in HK) of entrepreneurs who don't have a "proper" education yet go on to become admirable figures in the business or political sector. There's this belief that a well-regarded education path need not be the only way to go. This is something that I felt was missing when I first settled down in Singapore. It's always "Do well in your studies, or else..... (insert bad words here)). On the other hand, Hong Kong's education system has a host of its own problems as well and frankly speaking, there's a lot to admire about Singapore education system and I really feel that MOE is now taking some innovative approached toward the right direction (ie. more creativity in classroom etc).
In any case, I'm very aware of my status as an "overseas scholar" and the kinds of assumptions/stereotypes/privileges that're associated with it (especially since I went to a neighborhood school). As I return to Singapore in a month's time, I think that I really have to make an effort to get in tuned with the concerns/perceptions/world-view of the heartlanders. Not to say that I have to totally unlearn my 4 years exposure to John Stewart and the likes, but there's truly a myriad of going-ons in Singapore that I've missed out in the past 4 years, and I fully intend to catch up on lost times when I'm back home (finally).