Singapore

I really like the looks of this resort in Malaysia right outside of Singapore:

http://www.johorresorts.net/index.html

I think it would be a good place to stay in December up until the chess tournament (when we would need to move into the city). It costs about $90 for a studio, and the resort complex has lots of children's stuff as well as three pools and pretty much everything else you could want.

Singapore Sailing

3 day "Competent Crew" Course: http://www.rsyc.org.sg/seasports/sailing_courses.htm#keelboat

The Competent Crew Course is an introductory crew training course that teaches the basics of sailing onboard a sailing yacht. Upon successful completion of this course the sailors and participants will have sufficient knowledge and skills to be an able crew member on any sailing yacht. Suitable for both the complete beginner and those who have some experience of either dinghy sailing or cruising.

costs $550, is offered on December 4th, 5th, and 12th in Singapore.

I checked six marinas in Singapore, this is the only one offering a course in December.

Compare to Whitsundays sailing school, costs $1350 for five days:

http://www.sunsailwhitsundays.com.au/sailing-school/rya-sailing-courses/competent-crew-sunsail

Resort

On a secluded private island, Telunas Beach Resort http://www.telunasbeach.com/ has rooms/dorms available in December. It is a ferry ride away from Singapore (3 hours), in Indonesia. Eco-lodge style, no hot water, no tvs, no internet, no aircon, but flush toilets and nature/snorkling activities.

Dorms $50, rooms $120, stilted bungalows $160

Singapore Chess

Chess tournament in Singapore, December 24-30

http://singchess.gotdns.com/scf/general/Calendar2010.xls

TripAdvisor doesn't really list anything for these dates under $100 that sound okay. For $130-$150 there are some nice places though.

Lonely Planet's only reasonable sounding budget choice is Sleepy Sams: http://www.sleepysams.com/. A room with shared bath is $65, it is mostly a hostel, just a few private rooms. Trip Advisor says they aren't really private rooms at all, it gets pretty bad ratings considering Lonely Planet says it is the best budget option...

http://www.tripadvisor.com/Hotel_Review-g294265-d626257-Reviews-Sleepy_Sam_s_Bed_Breakfast-Singapore.html

Ibis Singapore on Bencoolen is the highest rated hotel under $150 ($110) available over Christmas and New Years. But it is 35km away from the zoo, I'd like to maybe be closer since I envision going there at least a few times (it is one of the best zoos in the world apparently)