Freedom is quite a tricky thing to balance.
More freedom = more possibilities and more entropy. Outcomes multiply. Consequences diversify. You face more permutations to choose from.You experience new things beyond the normal and expected.
Is that bad or good? It depends on how much freedom is granted.
We know about the problems incurred from the two extremes. Too little freedom and you get deprived of creativity and variety. You lose the feeling of agency, for the sensation helplessness. You have no control over the direction of your path. Your channels for expression become stunted or possibly cut off completely.
Too much freedom and you get lost in the possibilities. You'll take long to decide where to steer your course. You might not even decide at all. And even if you do make your moves, you'll still be left wondering what would really happen if you took the alternatives.
So how much freedom is "right"?
Singapore's an odd case for degrees of freedom. A little bit paradoxical, some might say. There are aspects of freedom in, say, practising religion or ethnic customs. But you face punishment from, say, maliciously insulting said religions/ethnic groups. You can choose who to vote for, but you'll probably land in trouble for strongly defaming the current Prime Minister or President.
In other words it's kinda like playing a huge game of pick-up sticks with millions of sticks. You get to choose which stick to draw out, but just make sure you don't move any other sticks in the process. And it's sorta inevitable: it's not hard to undo the structure holding the order in this society if there weren't the restrictive laws in the first place. Especially when the country's been burnt by past chaos before.
Though it doesn't hurt to reevaluate on whether the freedom dial for Singapore could be readjusted. Times do change, as do people and mindsets. Especially when globalization is rapidly improving with IT capability. Opinions exchange more rapidly. People have more standards to compare against. We get to see how other countries deal with freedom, or lack thereof... and how that turned out for those countries.
So how free is free enough?