A few concessions on emotionally-laden issues such as the 6th best healthcare system in the world?
I wouldn't want to live in Singapore, I don't think, but they have a lot going for them. Good health care, quite safe, reasonable commute times. We tend to apply a very one-dimensional (and I think downright fictional) idea of freedom to these discussions.
Sure, Americans are much better at freedom of expression legally speaking, but I promise you there are plenty of public libraries all around America where you couldn't find these books even if some of them would have the sense not to make public show of not carrying them. And if your family went bankrupt by paying for your father's heart surgery then while you are working your two minimum wage jobs you might not feel that liberated.
People in Singapore are generally satisfied with their country because things are working for them, not because they are fools.