Hi,
Can only speak from Experience in relation to medical. We went through Raffles Hospital in the City. Modern hospital (very impressed with it) with a fantastic doctor who took us through the first three years of my daughter's life - Veronica Toh. Very experienced - brought our little one into the world (2 months early so she needed lots of TLC).
I'm a primary teacher as well but can only comment on preschool I know through my daughter. When she turned 3 we sent her to 2 days a week at AIS. She now does 4 days a week at 4yo. The preschool puts so much into making it a great place you can't be disappointed. I only go there as a Dad but the things they do there are really impressive - I have taught in 7 schools in my life and this is the best preschool I have seen (again - not a sell job for the place - that is my honest opinion). Went to open day last week and parent interviews the week before that. We get regular weekly newsletters about what they have been doing with lots of pictures of the class. It is learning through play (which I am in favour of) - not rote learning or pressured learning by any means. My older daughter also went through preschool there and we were really impressed.
As to good complexes for families in those areas I think they are closer to the city. I live closer to the school in the centre of the island. Rents closer to the city are higher and I'm on a teacher's package, which is better than at home but nothing like being able to live on Orchard Road. I've been to kids' parties here and am absolutely gobsmacked by the opulance of some families' apartments or houses. The best thing to do is get an agent as soon as you get here and tell them your budget. My first place was a 120m2 new
condo and that lasted for two years. Lovelyplace but soon got too small despite the great pool area. We moved to a bigger 200m2 older place condo with high ceilings which was great. Initial rents were only 2000 a month then went to 3100 a month.
Good luck in your move and I hope you get a great place to live.