In Singapore's case, we don't need proxies - we can look directly at how the authorities respond to speech which tests the boundaries of dissent and taboo. Which they generally do with rapid and thorough censorship.

One of the things i found interesting about Singapore's censorship is that it's completely open. It is not itself secret, or a taboo subject. When i was there, i stumbled across an exhibition by local artists that was all about a major obscenity/censorship case in the 1980s that had had a big impact on the artistic community. The exhibition was in a public gallery, and i think had even been supported with public funds.

There's a lot of self-censorship going on from both Singapore's journalists and its people [1], mostly because there's a culture of fear.

Have a look at this recent case where a teen blogger was jailed for making offensive remarks against Christianity, and for circulating obscene imagery. [2]

[1] https://en.wikipedia.org/wiki/OB_marker

[2] http://www.channelnewsasia.com/news/singapore/teen-blogger-a...

Your logic sounds backwards to me. Restrictions breed creativity as people do their best to work around or within those restrictions. I would expect a government that is trying to encourage its citizens to be more creative to have draconian and arbitrary laws.