Thanks for write up AViking. Really insightful. To your point, much of the appeal of San Francisco is the ability to enjoy nature. It's hard to get motivated to go outside and enjoy life when it's -15 degrees with a foot and a half of snow.
For better or worse my commute would not involve a car. Rather, I would travel on a plane to a client location somewhere every other week and work from home every other week. I'm trying to make this work on roughly $80K which may be a slight strech.
It's hard to move back once you've sold. It's not necessarily the cost o f the housing, but it's the amount of house you get for the price when compared to elsewhere.
to the OP: It's going to cost a lot more than $900/month. You're going to love the price and quality of fresh produce. The women, too. So those costs are going to add up. Oh, and a Chicago GF and a SF GF means twice the number of gifts.
Maintaining 2 residences isn't cheap. Are you going to have 2 cars? How much stuff will you have to shuttle back and forth? It's just like the answer to the question of "Should I move to CA?"
"Yes, if you can afford it." Who cares if housing is expensive and taxes are high if you can afford it?
The difference between moving here and what I'm trying to do is that I don’t want my primary residence to be California. In a sense, I’m trying to have my cake and eat it to by avoiding the Midwest winter and still enjoying Chicago during the rest of the year.
I would keep my car back in Chicago and rely on biking, public transit, and zip car to get around. Ideally I'd like to keep the stuff brought to the basics like my computer and a month or so of clothes.