Hong Kong
Cost of Living: 3/10
Hong Kong is usually cheaper than New York, but not by too much. There are good deals, though-- here's a link to a studio right near one of the main social scenes for about 1350 USD:
http://hongkong.craigslist.hk/apa/2273783254.html . In general, spendier than most, though.
Safety: 10/10
Hong Kong is very, very safe.
Poker: 8/10 Online poker is technically illegal, but generally ignored. It's 38 miles to Macau.
Recreation: 8/10
Not too much in the way of sports, but beautiful tropical beaches are only a short ferry ride (less than an hour, usually) away. Can't really beat that.
Easy of Entry: 9/10
Super easy for Americans to set up shop in Hong Kong.
Political security: 7/10
Still maintains all the rules that existed under UK authority, though there is always the danger of China doing something crazy.
Women: ?/10
Beautiful women from everywhere in the world, don't really know what else to say here.
Hong Kong is basically New York City but more modernized, great weather, and incredible food. English is pretty widely spoken, they have an incredibly good subway system and its very, very easy to get back to the USA (direct flights to everywhere). Short trip to Macau for top level degeneracy. Plus, there's Disneyland. It's an unbelievably vibrant city.
Party scene is excellent with all the people working in finance looking to party hard. LKF is a totally sweet party scene, TST a little dirtier but also way fun, and it gets much dirtier than that. Something for all types.
I've traveled all over the worlds, HK is in my top 4 world places (the other three being west coast of US, NYC, southern france/spain/italy).
Andrew