Everything is tough from the local government, the tenants, super old buildings, ultra-depressed local economy. 

Why on earth would anyone want to buy property in IL, much less in among the most economically depressed places in the state?

., I worked the RE biz for almost 20 years and built up quite a good net worth, and almost lost it all on a hospitality property during the modern-day Great Depression.  

A flood, a serious depression, methane issue, a reputation, etc.

I took a few drives here and my lady said it looks depressing as hellYour flip looks real nice.

Or something near my family in upstate NY, however that market is somewhat depressed.

On a side note, I weathered the worst financial crisis since the Great Depression since all my properties were cash flow positive going into the deal.

What was interesting was the real estate depression wiped out the amateur and wanna be investors; the professional investors came in 2011 - 2014 and cleaned up.  

Even San Francisco and New York City are within a couple of hours of less expensive real estate, and even places where prices are depressed have solid neighborhoods fairly close by.Before You Buy Out of StateIf you're still intent on buying out-of-state, be sure to heed these additional warnings.

Would I do it again go through 2 major recession / depressions in RE?