During the past three months, I've traveled to Manhattan, San Francisco, San Jose, Portland, Chicago, and Miami for biz/personal trips.
I've stayed in mid-priced hotels. (Actually, non were cheap as in staying at a Best Western in the 'burbs. :-) )
Observations:
Manhatten: Used to love to go here. Now I find it crowded, dirty, and people are rude on the streets, but normal once inside. Least value per sq ft of hotel space of all the cities.
San Fran: Love the Wharf. Expensive, a homeless problem, past its prime?
Portland: Beautiful, had to fight off the homeless on every block as I walked. No sun the entire trip.
San Jose: Energy! Wonderful weather, expensive as hell. Traffic sucked.
Chicago: More I go, the more I fall in love. Clean, not crowded, people are friendly. Saw two panhandlers the entire weekend. Good hotel value.
Miami: Great food, the babes on South Beach were amazing eye candy. It would be too hot in summer. Condos expensive.
So if I had to move from middle of no-where Wisconsin where there are more cows that cars, I would pick downtown Chicago and try to find a condo overseeing a river or Lake Michigan.
I can deal with crowds and rudeness. I could waste a decade just going at my own pace from park to park and museum to museum and restaurant to restaurant. Just soak in all there is to experience.
Nothing on the island is 'too far' from Central Park, so I could 'waste' another decade with biking, walking, bird watching, people watching, sports, . . . then slow down to photography and painting.
Even if nothing changed [and face it, time marches on], I picture a good 1/4 century before boredom or wanderlust would set in.
I honestly think my philosophy and temperament are optimized for an urban life of wealthy [or at least the removal of wealth as an obstacle] leisure.
About the only thing I'd picture missing is woodworking. A bit too much to ask to haul a workspace and skads of raw materials into dowtown Manhattan just for my amusement. [Reply]
SF, followed by San Diego and Seattle. San Diego has the best weather, but less vibrant than SF. Seattle gives you almost as much as SF, but the weather would kill me. [Reply]
