On taxes, I'm sure somebody on HN knows better than me, but you are rarely 'double-taxed' under 200k as you say. The first 90k or so is exempt, plus any foreign tax you pay you can claim as a non-refundable deduction on your US return.

Singapore is an amazing country that is really geared towards making things easy for expats. The chewing gum thing is a bit of a red-herring. Ending up in jail for a minor offence is not something you generally have to worry about.