I think people who are saying that SG is family friendly have not lived in the outskirts of HK. I live in Tung Chung and we have plenty of space for the kids to run. I like the fact there aren't as many Chinese as in HK Island, it's mini India here and I find them way more sociable. And you're like 5 minutes from a hike.
SG is nice, but it feels gimmicky in a way. The food was great but it's because the person I was with knew where to go I guess. Business wise they are so slow, but HK people are slow when it comes to negotiation but faster at implementing.
It's all a matter of choice and personal taste. I like the chaotic side of HK, I feel HK has more grit. I don't know SG healthcare so I can't say but HK level is crap depending on where you go. Princess Margaret Hospital is a horrible place.
The North Lantau hospital is quite good but lacks specialists so you always get redirected to PMH. But they're extending it so should be solved soon.
For me the deal breaker with SG is the weather, I need some cold weather (though in HK it's been an atrocious summer), and I just can not handle Singlish.