Doug had been living in Singapore for about 2 years, and before that, lived in Malaysia and Hong Kong. I've been curious myself about the possibility of living overseas, so his was the right mind to pick. The weather? You get used to it. The benefits? A clean, safe place ideal as a base if you do a lot of traveling around Asia. The drawbacks? Not a lot of action; it's a pretty boring island.
The next night, I joined Doug again, this time with a group of his friends, all expats from such diverse places as Australia, England, Scotland, and San Francisco. A few beers later and I had them all sharing their wildest stories about living in Asia. One guy, a Scottish guy, had lived in Indonesia for a few years until the political turmoil had kicked in. He said Jakarta was his favorite city in Asia for all the same reasons that Singapore is his least favorite. Sure, he acknowledged the positives of Singapore -- the sense of safety, the cleanliness, the efficiency, the food. But he said something was missing. He had a hard a time explaining it, but everyone pitched in to try to help. Perhaps it's because you can't find anything bad to say about Singapore that makes you really try. But Singapore definitely lacks something. The prevalent opinion was that, due to Singapore's strict government control, the people lacked individuality and spirit.
Counterpoint
I doubt that many Singapore natives would agree that they lack individuality and spirit. One of the locals I met, Anna, grew up in Singapore and lives there now. She's traveled the world and spent her four collegiate years in Toronto, Canada. When I asked of her feelings about Singapore, she admitted that she does find it a bit boring, but she loves it nonetheless. The safety, security, convenience, and family values all add up to make Singapore a real home. She said she could never feel at home anywhere else, an attitude I heard echoed by many natives. Besides, she pointed out, its so easy to travel to nearby countries; you have your choice of where to go to find whatever it is you decide is fun.
To summarize, Singapore, I'd say, is a great place to go on a business trip, but it's not really a vacation destination. And it could be a great place to live, depending on what you're looking for. My suggestion is to arrange a 1-day layover there en route from somewhere in Asia to somewhere in Australia, something that I believe many airlines permit you to do. In fact, the next time I'm in Asia, I might try to swing by Singapore for another taste of those Sri Lankan Pepper Crabs.