In hk, parking in city is really tough to find and expensive. Also because cars are much cheaper relative to homes, cars are seen as much less of status symbol.
In Singapore, parking is still relatively easy even in town areas. Some city centre monthly parking fee is only $200.
Also due to COE and ARF, car prices are astronomical, so cars become a mobile status symbol, that is important to impress clients and girlfriends. Also because car prices are so high, once purchased, the car owners will maximize the usage every day. The public transport system is also deliberately operated above capacity to make it very uncomfortable, and thereby further elevating the car status symbol.
LHL cannot be so dumb as to not know the mentality. But his primary intention is revenue generation, so he opted for current system to milk the maximum out of everyone.