Please note that whatever that I have written are all based on my opinion:
I would attribute the lack of success to the fact that most Singaporeans have the mentality that local products are not very good until proven. Local celebrities didn't make it locally but outside of Singapore before Singaporeans will take notice of them. Such as Vanessa Mae, Kit Chan, Tanya Chua, JJ Lin and so on.
However:
http://english.pravda.ru/news/society/04-12-2005/72089-0/
"We" (not us, hence the quotes) are also chasing OUR local talent away. For someone who would forsake his "well-being of turning from a kid to a man" to pursue music had been "forced" to makeup for it due to "failure to serve his nation".
However, we also cannot overlook the fact that there are local musicians who "did make it", such as Dick Lee, Jacintha or Sheik Haikal. But their fame, "making it locally", isn't as "fabulous" as those who made it outside before coming back here. It is sad, indeed. But the truth is, there really are many talented musicians locally, when I was in NS, my understudy was a saxophonist, there was also a pianist who was a storeman. My warrant's brother is an Er Hu player in a Chinese orchestra, got another warrant with an awesome voice that can cover Hokkien and Cantonese songs. My friend is a vocalist who have been doing gigs and such. My other friend performs annually at Esplanade playing old Chinese music.
The thing is, we tend to "import more foreign talent than to breed local talent". I'm not sure if it is because it is "cheaper" or...something else, really. But I don't really know. In my opinion, when I see the Ping Pong Finals on TV for Olympic Games, I see as "China VS China" rather than "Singapore VS China". We really, really, really need / must / ought to invest in our local talents. Not by buying them but by breeding / training / educating / making / creating / -insert whatever word appropriate- the local ones. I'm not against bringing in foreigners or something, but I just feel we shouldn't bring them in to represent us. Bringing them in to train us is perfectly fine. Only when we broaden our horizon before we will learn to accept and get better. "Each mountain higher than the next" is a Chinese proverb. When we are expose to more music, we have a choice what we want to specialise in and what we want to focus on.
There is only so much we can do, BUT, there is so much more we COULD HAVE done. There are exposures to local musicians, but just not enough. We do not suffer from a lack of talent, we just aren't exposed enough. In a way, I'm glad our guitar heroes are coming to Singapore for local concerts (Iron Maiden, Eric Clapton, Pearl Jam (many years ago), Slash), but there should also be effort to help create talent rather than buying them.
It's not only attitude or aptitude, it is also attribute. "We" can only attribute the "lack of success" to "ourselves".