It starts with the immigration agent who sometimes feels the need to ask me questions for 20 minutes as if I were a criminal, there's the part where they get to look through all your social media accounts and hold you indefinitely, and then there's the thought of a traffic stop by a bored cop "degenerating"... it's tough to travel to countries like these when you're used to a polite government whose agents treat you, the foreigner, with consideration and like a customer.
For example, when I went to my PR interview, my medical checks had expired (and it was transparent I had hoped to get away with it); the lady very helpfully opened up a slot for me a few hours later and recommended me a range of clinics nearby to do the missing medical checks. A breath of fresh air after dealing with the French and other "first world" governments...
No CCTV in my street except for the hedge that borders the Istana 100m away. We do get the odd police car patrolling the perimeter, but since the President lives there and the Prime Minister works there, I can understand. As for the US, I've never been in a building with more than a couple storeys that did not have CCTV, so I'm curious about your frame of reference there (most of Singapore consists of 20+ storey buildings). I've never been in a US mall or office building without CCTV. The only reason my residential building in NYC did not have CCTV was because it was pre-war; it also didn't have working heating, and I'd rather have had both.
I do agree that Singapore is probably not the place to move if you enjoy a suburban lifestyle in a big house with a garden.
edit - here's something you can't do in the US: my friend and I bought a couple craft beers from a Japanese supermarket, then sat down on public benches in front of the Asian Civilisations Museum (opposite CBD and the Fullerton Hotel), cracked them open and sipped them slowly in front of the view.