As for Alexandria specifically in terms of regulations don't take advice from a public forum - look up the laws yourself and make sure you understand them.

For commercial buildings, be very specific - price range, $/door max, unit count, unit mix, part of town.

This is a highly regulated activity by the CFPB.

Here are a few additional strategies that might help mitigate risk if you decide to rent the property:Hire a Strong Property Management Company: While you’ve already spoken with some PMs, consider finding one with extensive experience managing single-family rentals in Cook County specifically.

Quote from @Matt Schreiber: I know this is a common question but wanted to hear specifically from investors or realtors that are seeing MLS cash flow for 2-4 unit properties.

LLCs are normal for CRE, so you divvy up the ownership interest how you and your capital partner(s) see fit.What's your specific question? 

You can find multiple good deals, we are growing at a very fast rate with multiple industries coming here. 

You have to weigh the benefit of the insurance claim payment versus potentially having your carrier cancel you and perhaps get black-balled by the insurance industry.

Are there specific tools, presentations, or approaches that help them feel more confident in taking that first step?

Specifically, what research results told you these were two good cities to invest in?