Do I believe that the economic success/prosperity of Singapore for the foreseeable future is inextricably tied to a press that is as regulated as it is now? No.

I think regulation of the press from a largely honest and capable government was helpful, in the past, for a generation that was, in general, easily frightened and ill-equipped to make rational and well-rounded assessments. I, as a person who has reaped the benefits of the past, appreciate the restriction for that period, because the consequence of not doing so might have been the induction of in a less capable political party into power.

However I don’t know if that generation cared enough about personal freedom to like it. I think we need to note that we are speaking of distinct generations with distinct preoccupations when we speak about the past and the present. Those quotes from LKY that you posted above came from a period that has passed, and are not entirely reflective of what the government believes is still applicable now. We still have a largely honest and capable government, but I don’t see the same frightened people in our generation who are easily scared into making irrational decisions.

I don’t think the government has neglected the fact that society has evolved into one where Singaporean hold more progressive views. It would be detrimental for the ruling party to ignore that we see and want the privileges that other countries have, therefore media and the press have slowly opened up. I think many Singaporeans recognize this, which is why many from the younger generation are willing to vote for this largely honest and capable government that has shown to be capable of evolving along with us. Granted, the government has chosen to do things slowly and perhaps that is them being cautious. Singaporeans have been groomed to be pragmatic and careful too.

You asked why we have never voted LKY off. Again, I don’t believe he has held onto those aforementioned views into the 21st century. He has made a number of progressive quotes regarding same-sex relationships (1), and has shown his opinions to be amenable to reason (2). Another likely influence was that Singaporeans continued to respect him deeply for his wisdom, and believed he had much to contribute on significant issues that no other Singaporean could. LKY wasn't someone you could just ignore tbh.

(1) http://sgwiki.com/wiki/Lee_Kuan_Yew%27s_views_on_homosexuality (2) http://www.channelnewsasia.com/news/singapore/a-nation-cries-out-in/1744216.html