Not much to add to what everyone else has said (on previewing, apparently I have a lot to add, but I'm posting anyway
), but some random thoughts.
Many of us, I'd imagine, thought during planning that we'd prefer a house (they call them landed properties here) rather than condo life. Certainly for your first lease I'd DEFINITELY go for a condo. You will benefit from the random people around you, and it will help with the feelings of isolation we all get from time to time. We avoided the big ones, but it's very possible to have great facilities even in a small condo.
If you can, get a property agent - it will help you find what you're looking for and will help a bit with the landlord situation. You will hear horror stories of end-of-lease. Don't believe them all, but be aware that the balance of power in the landlord-tenant relationship here is firmly on the side of the landlord, and make sure you are very diligent when you move in with recording all details of the property and taking photos.
We live East so I'm biased, but it's fantastic this side. You're not in the proper River Valley expat bubble, which can be a bit oppressive IMO. It's pretty suburban this side, you get more property for your money and it's green as green can be. Agree with others, though, choose the school and live near it. We are walking distance from my children's schools and it saves hundreds of dollars a month. We both work in West/central and have a 20-30 min commute which horrifies our local colleagues, bless them.
Do consider EtonHouse Broadrick if you're coming East, it's a fantastic little school - tiny, family atmosphere, not huge fantastic facilities, but a great place. My oldest came from a tiny village primary school in the UK and EtonHouse was the closest international equivalent we found.
We can't afford a car and rarely miss it. My compromise was that we travel most places by taxi and it's still cheaper than having a car.
If you're intending to work, I don't know how anyone manages without a helper, though. Wrap around childcare is virtually non-existent here. The helper thing seems weird from the outside, but you can make it work to suit yourself and I'm glad I caved in the end - I wouldn't be without her now.
If you haven't already and you're on Facebook, join the groups: Singapore ExPat Wives, Real Singapore Expat Wives (don't ask, there was a schism, it was full of drama) and there are some local ones too. Tune out the noise, practice rolling your eyes at the entitled nonsense and you'll find a useful community.
All in all, this is a very easy place to live. Everything works here and although you'll find some things that do drive you to distraction, it's friendly, open, centrally located and safe. You will be busy every day of the year if that's what you want, and you'll be within 7 hours flight of some of the most amazing places in the world. It's not home to me, and I don't think it ever will be, but it's a great place to spend a couple of years!