i think a lot of it has got to do with national pride, and Singaporeans' perception of their own country, people, culture etc... If Singaporeans are ashamed of their own people, or do not like their own country, i think it's very hard to get them to appreciate their own work.
We're a young country. We don't have the advantage of hundreds or thousands of years of history and foundation which, in my opinion, are essential for any form of sophistication or well developed culture.
Until someone invents a way to make good art out of the way Singaporeans currently feel about themselves (take advantage of our own perception), locally produced work won't be appreciated.
That's what i feel..
Edit: Forgot to thank James for this interesting video! Thanks for sharing!!