I thought I was going to be able to watch this long ago but I couldn't interest my wife to watch this while she was in Singapore with me as she is not really into Romcoms. Overall, this seemed a pretty standard Romcom done in a different setting. As far as how locals are represented, well, it seems exaggerated and you don't really see many average people expect in the background. The most average main character being portrayed was Rachal's best friend, Awkwafina and her family. Though they are already are what most would already consider crazy rich expect they made them see a bit classless and tacky, perhaps to separate what it is to be very rich to crazy rich? Perhaps that is my biggest complaint, few of the people that are on the outside of this group, are played as tackless, like the actress that one of the guys is dating.
Most of my local friends have enjoyed the film, while exaggerated, many parts ring true. Perhaps around the expectation of their family on what career to follow, who to date, and where to live. While a lot of locals go overseas for schooling, most of their families are expecting to return when done. My close friend "jokes" that his kids are not going overseas for school out of fear they may stay. One area that is probably spot on is that most locals that have been overseas for a while are always going to search out their favorite hawker foods as soon as they land. I have a few Singaporean friends that live in the US, when they come back it is all about going out for favorite foods.
But overall? You get some great views of the city if you never have seen it, but not too much of the heartlands where most people like. I didn't really find any laugh out loud moments but a few that may have choked me up a bit. And the Majong scene towards the end was really well done.