Then generally the best advice is to buy in the best area that you can afford, even if the cash flow isn’t as good in year one you will get more market appreciation in equity and rent growth in the better area.

So you can buy a four flat, live in one unit and rent the other three, but you have to live in one unit on the site. 

He usually buys in C neighborhoods and has to do heavy rehab, but he's a construction guy that also runs his own property management company, so it's 2nd nature for him.

Investment Info:Other buy & hold investment.

Since you know what you need to buy it at and an average rehab cost, I would say $50-70k for a cosmetic flip, set the ARV based on the sample you choose and doing comps and ask them if they would invest in a deal similar to this. 

Quote from @Veronica Mitchell: I'm looking to see what are some of the multi-unit in and around Chicago area to buy in? 

Last thing to consider is if you are buying a new home, will you want to do 100% financing and will you have the remaining bonus entitlement to do so.

Buy a 2-4 unit, close to home.

Would love some feedback before I make the initial buy in. 

Buy-in is often more conducive than other more saturated markets and there's such a wide variety of options to choose from.