Singapore's rapid development is quite evident in the shocking contrast between generations when it comes to education, career possibilities, etc. Schools certainly have progressed; I'm sure not that many years ago noone would have cared whether a school was "branded" or not. (I think the entire branding fetish is a sign of decadence and decay anyway, but that's just my personal opinion.) What I would caution against is calling Singapore, or any country, "developed", as in past tense/completion form. Development is an ongoing process, resting on your laurels means falling behind.
In all likelihood, this is not due to "development", but simple inflation. In my childhood, similar prices were common, even in a then-already-"first-world" country. A brand new VW beetle cost less than S$10000 (assuming today's conversion rate) ca. 1980 in western Europe, and a used one could go for a few hundred. Of course, the exchange rate back then may have been rather different, but the prices for some basic commodities have certainly multiplied by huge factors since when I was a kid.
To go back to the topic of the thread, "branded" or "elite" schools may mean kids get more possibilities shoved up their rear ends. But kids from "normal" neighborhood schools may have a plus in their resume, since if anything they made it to a given level on their own, with less help, and likely driven by higher motivation. Otherwise, noone, at least in my work environment, seems to care about what primary/secondary school or JC one attended. And if there are more kids who "made it" in the "elite" schools, one has to wonder if this is due to the school, or simply the fact that the better kids, who would have made it at any school, tend to end up there.
Actually, a job applicant who went through the polytechnic route before attending university has quite an advantage - he/she has practical, hands-on knowledge and experience, whereas many "prestigious" JC kids who went to university are excellent at scoring grades and regurgitating memorized facts, but not necessarily at working on real problems. (Some even seem to be shocked that they have to do "mundane" manual tasks instead of making Nobel-prize winning discoveries straight away.) At least in the company I work for, we look at skills and personality, not paper qualifications when we hire. And since diversity in the staff profile makes it much more likely that there is someone who knows how to solve a problem that pops up, we tend to hire people with nonstandard CVs, rather than having 100 clones of the "standard Singapore scholar, model 2007" who are all excellent at the same thing, but all equally helpless when they encounter something that they haven't seen before in their books (which, in the real world, is the rule rather than the exception).
This entire "elite school" thing is very Singaporean to me - a lot of stress and hype about nothing. What becomes of oneself is maybe 5% the school, but 95% yourself. And maybe instead of going to all those tuition classes and spend the rest of the time on computer games, kids should get out more so that they see a bit of reality. It was quite sad to see a local young dad struggle to tell his kid that a bird was an ostrich or a peacock at a pet farm near Seletar when in fact, it was a casuar [edit: the name cassowary appears to be more commonly used], a very distinctive local (!) species. One will gain a much better understanding of science from observing and _experiencing_ nature than merely memorizing formulas.