I went to the first one in 08. Let me just say it was a pain to go around for me – literally! My ankle had barely healed from a sprain, but all the pain was worth it. ;)
But it was also a pain to go around because there were so many people, and thus the MRT (which is the best way to get around Singapore most of the year) was jampacked. I hope they’ve improved the situation over the past two years. If they have, it’s the best way to go, because the streets in that district would obviously be closed.
The best place to go at night would be Clarke Quay (which is up all night, especially that weekend). It has great establishments, and a great view too. Try to pass by the Raffles Hotel too – the last time we went, the reception parking lot was obscene – the cheapest car being a Mini Cooper, and the majority of cars being shiny red Ferraris. Not to mention they created the Singapore Sling.