My dd1 was 3 when we moved to singapore and I was pg with dd2. She was breech and late so born by cs (there is not an obstetrician who will contemplate a breech birth in Singapore). Find yourself an obstetrician (mine was dr Paul Tseng, hugely popular, goes for less medicalised options, lots of expats use him and I can recommend him). See if you can join the singapore expat wives group on fb (pm me if you can't and I can invite you, they've just tightened up). They will be able to give you more recommendations.
Births in singapore are very medicalised, you'll often get an epidural on admission to a maternity ward (my friend joked that they were ready for hers in the car park) but care is great and as this isn't your first, you'll be a bit more clued up about what you want.
Definitely make sure you have insurance for everything, you, the baby, the birth etc. its a very expensive business! Otoh, I had a scan at nearly every check up (weekly towards the end) as dr Tseng has ultrasound in his office and insurance paid, it was brilliant!
There are lot a of good groups. Mother and child in tanglin mall is good, they have uk midwives and health visitors if you have queries but it's super expensive (gbp50 for a quick check up with dd2). There is no midwife or Hv system in Singapore, you're basically on your own once you are discharged apart from pediatrician visits every so often. Look at new mothers support group too, lots of meetings, talks, play dates and coffees for mums with bumps, babes and toddlers, buy and sell forum. Been running for over 20 years (I chaired the group for 4 years so maybe biased but it's a great community)
As long as you've got insurance, you'll be fine.