Answer:
I think I would prefer a poor genuinely democratic country. I am not very impressed by great material wealth, so that is not going to persuade me to keep my mouth shut. Just think of living in Singapore, I would hate it.
Also It depends on how poor, but I think on the whole poor in a democratic country is better. Lots of rich people, I believe, buying property in other countries because they don't trust their government not to take their money and/or put them in jail. That's the disadvantage of non-democratic governments, they can be extremely arbitrary and you don't get much in the way of appeal from them.
Hope this helped?
~Heaven~