Midwest

Like any big city, Chicago has its ups and downs: friendly people, Millennium Park, high taxes, and expensive parking lots. But as an investor, there’s no place I would rather be. I moved [...]

The Chicago real estate market can be challenging for new investors due to the constantly changing landscape. Yesterday’s up-and-coming neighborhood is now the most expensive market in the city, [...]

In my years as a real estate investor, Chicago has proven time and time again to be brimming with profitable opportunities and great people. Overall, the Chicago investment property market is on [...]

My best friend’s son, Dave, recently started investing in real estate, and a few days ago he invited me to lunch at Mr. D’s so he could pick my brain. I love mentoring new investors (and steak [...]

When I first started investing in real estate, the hardest part was finding leads on good investment properties. The Chicago real estate market is highly competitive and full of ambitious young [...]

One thing that real estate investors love to do is analyze the housing market in an area of interest, and I’m no exception. Every minute spent learning more about the environment you plan to do [...]

I’ve lived in Chicago my whole life, and over the course of my 20-year real estate investing career, I’ve bought and sold dozens of properties. I know the Chicago real estate market like the back [...]

In an effort to find the best real estate investments in Chicago, an old colleague of mine, Josh, came to me for some direction. He’d tried his hand at investing in the past, but quickly gave up [...]

All cities change, but for those of us who have been in Chicago real estate for a long time, the changes have been dizzying. I got into it in the early ’90s—when the South Loop was still a no-go [...]