@David Davis, you are in a great position! I will say start by buying a 3-4 unit building through house hacking, meaning living for free. To use leverage, take an FHA loan with only a 3.5% down payment, and if the property needs work you can use a 203K FHA renovation loan, meaning you are borrowing from the bank the money to fix up the property too in the same purchase loan. So for example, if the purchase price is $400,000 and the renovation loan $100,000, total will be $500,000. You'll need to put down only 3.5% of $500,000 only $17,500 and the closing cost you can either negotiate the seller to pay them or bring them from your pocket. The trick to remember is that 75% of total rents have to cover 100% of the mortgage, tax, and insurance!
Buying a 3-4 unit will help you lower your monthly expenses as you'll pay no more rent and get a lot of depreciation/tax deductions while building wealth as the moment you become a landlord the IRS sees you as a small business. When you buy owner occupant, as you probably already know, you'll have to occupy the property for at least one year, after that you can purchase another property with a conventional loan, 5% down, which could be a condo, townhome or single-family home that after you move out will also give you positive cash flow.
Meanwhile, as you are building your savings and positive cash flow you can start buying properties with the BRRRR strategy, meaning Buy - Remodel - Rent - Refinance - Repeat.
So buy a property that needs work at a discount, remodel it with the strategy that when is fixed up the value is at least 30-35% more than what you owe on it including the downpayment you already used. When refinancing pull the cash that you used as down-payment back out and then start again with the next property.
If you have more questions about these types of loans, you can reach out to @Jesse Byrer, as he's an expert in Chicago.
Good luck to you! What great timing to buy in this market at a 3% interest rate!