Marc- I am not a long term owner here in Illinois. I am only a relatively green flipper. I do, however, have a long history of living in the Midwest and 30 years of professional experience in finance and investing. IMHO, Illinois is in a death spiral that is largely the result of the one-party progressive system that is well known for its patronage and corruption. Politicians here seem to have a never-ending thirst for revenue, but often enact legislation that drives away the source of revenue. A perfect case in point is the new Cook County beverage tax, or the silly minimum wage law going into effect shortly. Drive a few miles out of the county and shop there, or locate your business there - not a hard concept to understand.
In contrast, Wisconsin has made tremendous strides reducing waste, bloat and taxes, and the results are starting to show. Over the long term, how can housing demand keep rents growing when the population net migration is negative?