@Justin Repp Personnally I don't think it's a problem to buy it, live in one unit and rent the others however the City/Town will:-(So I'd look at what it takes to accomplish the goal of a making it a 3 family, deduct it and your profit from the listing price and move ahead.I've done two on the North Shore, not exactly like this one, so I'd be glad to meet off line and talk more about it.

Based on what we discussed offline, I wanted to see what folks were getting, as many lenders I've spoken with won't give precise #'s without an application on my part.

As Eric La Pratt had said the meet-up on the north side of Chicago that he was talking about is a great place to meet people offline and start to build relationships with people in the area.

Best of luck and it would be great to learn more (possibly offline) about your plans and aspirations for real estate in the area.Kirby

We would love to speak more offline about how we can work together moving forward.

At this point it's enough for me to know it is theoretically possible depending on how the deal is structured, and I'll follow up detailed questions with a 1031 exchange facilitator offline. 

Contact me offline and I can send you some links.

Let's talk offline

@Melissa Nevich If you want someone to but in for you, or just talk further off line, send me message/colleague request, and we can chat.  

Let's talk offline!