I believe that a strong economy will ease the transition from an autocratic society to a more liberal one. Singapore appears to be loosening up socially.
It will be difficult, because their strong economy is directly tied to the fairly non-democratic society. Its main competitive advantage are the large quantities of cheap labor it is surrounded by, which it manages very carefully with a top-down system of residence classes. A Singapore with more equal rights would be a very different one economically.
One could argue that Singapore's competitive advantage is that they can attract top talent from neighbouring countries by offering a better quality of life - which, anecdotally, is the case among my friends - in which case a Singapore with more equal rights might actually be stronger economically.
Some of that quality of life is dependent on having cheap labour from neighbouring countries (and repressing any protests). Who washes the laundry quickly and efficiently at a low price, and serves at that nice restaurant?
For tech jobs talent, the immigrant status is different of course.
I'm not telling Singaporeans what to do, this is just for the note.