@Arthur Panagopoulos - The property taxes are fairly low, no income tax on salary and wages, 3.2% unemployment, decent population growth, affordable, good for cash flow, decent weather, cap rate in th 6-8% range.  

In addition, there's the weather to contend with.

Hopefully this doesn't come off too harsh... but when people get so caught up in the physical aspect I have to ask why?

The weather is sometimes a reason for southern cities, not for MKE.

@Bill Crider Yes, the weather is awful!

And a few days before the closing the weather turned warm and the smell cme back.

2) Since I am on the east coast, can snow cover up problems with homes (cracks, yard issues, etc.) and make it harder to inspect them or does the colder weather make issues even more apparent thus easier to detect?

The next strategy is how to finance for that second home - we debate weather to do a 5% or 20% down, of course a 5% is more doable (we have savings), and a 20% takes too long to save for.

Only licensed agents associated with the MLS can open the boxes, and they are satellite tracked so the time and which agent opened the box is immediately available (well, cloudcover and weather not withstanding). 

So on places with good weather or close to vacation spot will attractive a lot people who can work from anywhere.