Which is sad cause I do love tropical climates but just not the insects, reptiles and other creatures that come along with it.

The Lower your tolerance for Risk, the more you will not do things to achieve that luck, such as buying at a negative cash flow.HOWEVER, if you do your Economic Analysis and apply your Future Value Financial calculations using a pro-forma 10 year projection business plan spreadsheet, you are looking just for DUMB Luck.BUT, when you build your analysis, apply intelligent assumptions, such as checking with City Planning to find out what Projects have been approved, finding out the future outlook of the industries that support jobs in your area, looking at migration of people (ie... it's fairly predictable that NYC will have a NET inflow of people especially due to Climate Change.

I also think Minnesota has a friendlier business climate as well.

Chicagoland is a huge area with an incredible variety of locations and investment climates.  

An old 4 unit in a working class hood may be a lot less liquid then a beach front rental in a warmer climate.

Its probably a little pessimistic in a climate like @Bob Bowling's but its not too far off.  

Originally I'm from Minnesota, but I tend to gravitate to warmer climates. 

I don't want those dimes going to the utility company instead of me.ETA: It matters a lot more in cold climates.

@Nick Gerli I would argue with current economic climate, the A or B areas are undervalued.

I'm in San Diego with a climate that lends itself to outdoor living.