@Marc Latreille Oh man, I have to catch myself from writing an essay so I'll try to keep it cliff notes version.
Investors from all over the world figured out how cheap Chicago was about 5-6 years ago and there has been a buying frenzy up until about a year ago. I've personally done closings on probably 900 units just in the south side areas you linked and we still get inquiries every day because of the low prices and cap rates. Chicago is a world class city and strong jobs, transportation, and investment opportunities that has been under attack from investors and the government for the past year and its caused things to slow down.
1. Expectations - Global investors around 2010-2012 figured out you could buy up properties all over the south side and easily hit a 15 CAP, which set off a buying frenzy. As more people figured out the prices were cheap and the inventory naturally was bought up, it left fewer properties asking more money. The same properties we bought at a 15 CAP are now asking at a 7 CAP. No one is buying at that number. On the north side, a 7 CAP is great because generally you don't have rent performance issues.....
2. Rent performance - You have to be careful with some of these buildings. The south side is block-by-block. One block can look great, the next is riddled with drugs and gangs. There are some wonderful properties that are filled with horrible people and you will never see a single rent payment on time. Trying to clean out the buildings is a nightmare, we've tried. If you go into eviction, you should miss 5-6 months of rent easy and forget trying to collect a judgment. If you have to remove them, the sheriff won't execute an eviction if the temperature goes below freezing because it's inhumane. Once we get into the dead of winter, the tenants know they can play the system.
3. Government - The State of Illinois is fighting over a series of legislation aimed at commercial property owners that have profited from everything above. Rent Control was proposed but didn't make it out of the legislative committee (that is mostly Democrat) mainly because they weren't prepared. They are preparing to go back at it again next summer. When the City of Chicago had a gap in the budget, they looked at raising the transfer taxes for properties over a million. If you sold a property worth $3.1 million, your transfer taxes to the city would jump from $22,000 to $79,000. It didn't get passed, but Chicago always needs money and it may come up next year again. We are also dealing with a potential jump in real estate taxes for all commercial properties that is still unknown, which is scaring investors.
In my opinion, there are still amazing opportunities in Chicago, but all the negative press is pushing people away. Chicago, more than any other city, requires having boots on the ground team members to keep you from making a bad buy. It's extremely easy to over pay for a property in Chicago or buy on a bad block. A lot of investors won't admit the reason they don't like Chicago is they made a bad buy and got burned. A brick duplex for $40,000 is great, but know it might cost $90,000 to make it habitable. If you are serious about investing here, get a team together and make sure they have your back.