Also, the largest group of people "enjoying" their isolation is uni students returning from overseas. Likely not the poorest folks in Singapore, but more ramen than caviar in terms of the personal wealth spectrum.
1) There is no lockdown / shelter-in-place / quarantine in Singapore. Normal residents can go about their daily lives as usual, with a few restrictions for crowd control and a lot of temperature checks.
2) Being stuck in a hotel room for two weeks, no matter how luxurious, is a lot less pleasant than being able to carry on with your life as usual.
3) This is done because returnees from the US and UK pose a high risk to Singaporean, and if they are quarantined at home with family that risks spreading it to family and then into society.
Writing this from a cafe by the river in Singapore, not locked into my apt. It's a beautiful day today with lots of people walking around.
Would be even cooler if they found a way to maximize personal liberties too (referring to the freedom of expression, religion and sexuality). It's hard to see why it couldn't just embrace those. I doubt these freedoms are the gateway drug to democracy they fear it is.
You do need to follow the rules though or face incredibly harsh punishments for any crimes (including drugs etc).