Cruz thanks for the pointers. As I said I am pretty sure that I will not be able to get a corporate job right away after my training ends but after a few hundred hours in the C-130 and an upgrade to Aircraft Commander, I am sure it will be alot easier. In addition I believe that I may be hitting the industry at a time where the needs for pilots has become critical.
As far as moving to Chicago and the reasons. We have numerous friends that live there and go to the city frequently. It is possible to live on 45k a year as I have several friends doing it just North of Chicago. We want to move because of the opportunities for my wife, closeness to Michigan where a majority of are friends are and the overall personality of the city.
As far as weather goes, I grew up in Buffalo, went to school in North Dakota and lived in Western Michigan. I am pretty sure Chicago does not have anything new that we have not already experienced.