Actually, I once tried to pick amony the following cities for one of my second homes:
o Sydney
o Vancourver
o Toronto
o Hong Kong
o Singapore
o Munich
And, I did travel and stay in these cities for some time too before I made my final decision.
My decision was based on:
o Nice weather during Fall and Winter
o I am from San Francisco Bay Area which is cooler and nice in the Summer but rains in Winter. I can always return home for Summer.
o Safe. Safety was my number 1 concern.
o Food. Asian foods (especially, Chinese, Japanese, Korean, Indian) suck in San Francisco. But, I can't live on Asian food alone. I need good bakery and bread. Hong Kong has the freshest baked goods around.
o Nice to be able to fly anywhere and anytime inexpensively
o Taxes of any kind. Lowest in Hong Kong
o Outdoor (water) activities.
o Transportation and costs. Toronto is the lowest but you still need a car there.
o Emerency health care cost.
o Night life.
o Something to do if I get bored.
o Easy access to world financial markets.
o Opportunity to make more money if I decide to start another company (high tech) in the future.
Singapore the worst political system, IMHO. It is almost like living in a Communist country. Toronto is too cold in Winter and too hot/humid in Summer. Munich is too "grey". I decided against Vancouver because I can always return home to sky in California and it does not give me any extra dimension. It came down to between Sydney and Hong Kong. Costs of all kinds (living, transportation, food, etc) swinged me toward Hong Kong.