I have been living in Singapore for 4 1/2 years and livng in Asia
off and on since 1984 (mostly on).
Great sailing communities here.
Singapore cost of living is down somewhat with the recession, most notably housing, which went mental over the last 2 years. Goods and services are still quite high.
Feel free to PM me with an email
address and I can send you my "expat primer" - I manage a diverse group of expats and have some insight to structuring of expat asignments.
There is also a web site that is pretty specific about living in Singapore. There are a lot of trolls there but if you can sort out the random noise
there is a lot of helpful advice.
ExpatSingapore - ExpatSingapore Message Board - Index
As far as living aboard
in Singapore it is an option but it is one that has been "discovered" and can be quite pricey. The marinas
are not very convenient to the Amercian school
located on the northern side of the island and with a pre-schooler that could become an issue.
The other issue is that the boat market is very small and finding a suitable liveaboard
boat to purchase
can be time consuming. You may consider sourcing the boat from Thailand
where the market is slightly larger and sailing it down.
One suggestion is to make sure the package has as much temp living in it as possible. There are outstanding service
apartments available but they are pricey as well.
If you get a "look see" trip all the better.
Final thought is to obtain a 1 year lease
on a condo and get the lay of the (boating) land - your term of assignment may make the whole idea of buying
a boat, living aboard and selling out, somewhat of a money