In Singapore, we just have employment laws that aren't as strenuous on the employer, so there's less need to 'game the system'.
Oversimplified: legally everyone is already a gig worker in Singapore.
Seems to work out fairly well.
This is also closer to how the system worked in eg the US until a few decades ago, when it was easier to get a job just by walking into the shop and asking and also work your way through college etc.
I remember, Slatestarcodex had an article about the dangers of outsourcing your social welfare to employers.
I feel this point is getting lost on you but Singapore has a vastly different culture to America. The fact that Singapore doesn't need to "game the system" isn't because there are fewer regulations. It's because it's a different culture.
The reason America needs legislation is because American companies have a culture of abusing a free market.
What works for one country doesn't automatically work for another.
Singapore is mostly made up of immigrants from China. Remember, China is the place where we like to complain about 'companies abusing a free market' even more than in the US.
Oversimplified: legally everyone is already a gig worker in Singapore.
Seems to work out fairly well.
This is also closer to how the system worked in eg the US until a few decades ago, when it was easier to get a job just by walking into the shop and asking and also work your way through college etc.
I remember, Slatestarcodex had an article about the dangers of outsourcing your social welfare to employers.