I don't live IN the Woodlands, but very close, and I've been here for long enough to hear all the pros and cons (10 years), SO.
If you are very active at the school, you will like living in Woodlands. If you live in the Orchard Rd. area, especially if you are not right near an MRT station, it will take you over one hour to reach the school, unless you use a taxi. That will be about $15 one way, and will not be easy during rush hours or rain. (They've told you it rains nearly every day, haven't they?) Other areas are closer, and if you have a car of your own, you will be able to get there in 20-30 minutes from just about anywhere.
IF your husband has to commute by MRT to downtown, or has to drive downtown or out to Jurong area, it will take him about one hour in fairly stressful conditions every morning. Since that is a daily occurrence, and your kids will be riding a bus in any case, it's not worth it unless you will be there a lot (In my opinion). If your husband travels a lot though, he won't have the commute that often, and it may not be a factor.
The Woodlands area has had a moderately high and consistent problem with burglaries. There have also been a few attempted kidnappings of elementary-age expat children in the area.
The plus side is having a neighborhood full of other Americans, with lots of kids to play with. They have block parties, great trick-or-treating, and caroling at Christmas. Most of the houses are huge, and many have small swimming pools.
You can find many of these things at the big condos that have lots of expats as well. If you plan to get involved in any other community organizations, such as the AWA, or spend a lot of time at the American Club, or get yourself a job you might not want to be so far out of town.
