Hey there!
With a budget of $50k - $100k for down payments, you're in a solid position to get started. If you’re looking at single-family homes or 2-4 unit multi-family properties, your budget can go a long way, especially in the Chicago suburbs.
For single-family homes, you could potentially afford 1 or 2 properties, depending on the price range of homes you're targeting. Multi-family properties may allow you to buy 1 higher-priced one, or you could look for a mix of smaller, more affordable multi-family options.
As for diversifying, I agree with your instinct — spreading your investment over a couple of properties can reduce risk and give you better cash flow. However, putting it all into a higher-quality property might give you more stable returns in the long run.
In short, if you can find quality properties that meet your criteria, diversifying could be smart. But if you come across a great single higher-end property, it might be worth putting more into that.
Good luck!