@Ami Sapir, I very much doubt that I can easily convince you to become a small-scale hands-on investor, let along go whole hog and get your contracting license and insurance like me. But there is certain something you CAN do in this time period if you have any sense of wanting to own rental property, wholesaling, or organizing quick renovations for resale (flips). Illinois is a judicial foreclosure state, just like Pennsylvania. That means foreclosed properties in Cook County have to go through the court system.
With at least two years to wait before you start doing any sort of your-money deals, you can definitely start studying up on foreclosure procedure in Cook County. Many real estate advisers and gurus don't tell you much about foreclosures because laws very from state to state and county to county so much, but learning how the foreclosure process works in judicial foreclosure states and specifically, in heavily populated counties like Cook County in Illinois, is really a great way to target distressed property, from the initial filing of foreclosure through the sale all the way to picking up tax derelict properties or REOs (bank owned properties). Because it's such a technical process, and involves understanding multiple points of law, court process, property valuation, and how loans are made and satisfied, lots of investors prefer to stay far away and find acceptable deals through the MLS, bandit signs, or other lower-return moves. The perception in much of the general REI community is that foreclosures are for high-risk gamblers, which, at least in my county, I've found to be a complete lie. The most successful buyers at foreclosure auctions are the most informed and decisive ones, just as they are everywhere else.
Learn the web sites and county offices you'll need to quickly spot an obvious cloud on a title by yourself, learn to investigate individuals through public records, learn the tedious auction procedures. Go to the sales.
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A second thing you can do is figure out WHERE you're going to operate, if you're going to operate locally (which has significant advantages). How is the real estate landscape in Cook County changing? Which areas are on the rise, and why? What are the forces driving gentrification in some areas, and what's the history behind how the slums became slums? Drive around. Look at these neighborhoods. Check their demographics. Get information on public transportation and snow removal. You can start by going to take a look at Winthrop Harbor, Beach Park, Homewood, and Flossmoor. The Interwebs tell me they're the four hottest suburban markets in Chicago. What are the school districts like? Why do people want to live there and not in other places? How do you find out who owns a house, what they paid for it, and when they bought it?
Traditional investors train their memory on their target areas this way. There's nothing to stop you from starting now, while you still have plenty of time before you make your first moves.