Any place with people can be a good rental market. All of it depends on your risk level and the return you want to get. You get a property for $5000 and you would probably get a good return, but are you going to get good tenants? If you have to put in more money than it is worth, then it probably is a risky investment. Chicago is a huge place, so it sounds like you need to talk with someone from the area to narrow down your options.
Process is the same. It's only different for the broker representing you, different submittal process and forms.
Usually the Fannie Mae home anywhere give 1st option to purchase to owner occupants, after 15 days if they have not received a qualifying owner occupant buyer then it's made available to investors.
Hope this helps!
If you are looking to finance the property you should speak with a lender first to complete the pre approval and determine your price point. This will help you assess the ROI for the properties that you are considering.
I do have a lot of experience with Fannie Mae Homepath and Homepath renovation financing if you need assistance
Senior VP of Mortgage Lending
773 290 0455
Visit the website http://www.homepath.com/search.html?st=IL&ci=Chicago
for a first look at inventory that may not yet be in the MLS.
Be smart, use an agent who knows the neighborhoods and will make sure you get a fair price.