House Hacking: Looking to do this for first time, any feedback?

[Roderick McCleary]

Hello Chicago BPers! I'm a newer investor and got started all thru the power of the BP Forums about 1year ago. I'm currently looking to do my 2nd Multi-Family deal, this time in Chicago where I would "house hack" by putting down 5% on a 3 or 4 unit building (looking like 3 unit is most realistic). Any advice or war stories to share with me? All feedback and comments are welcomed.

Background:

I own my primary residence 1br/1ba in WLoop and would be looking to move out/rent it for 1yr to move into the new 3/4unit building. After year 1, I envision moving back into my WLoop so I can rent out the unit I was living in at the 3/4unit which allows me to secure a low-Interest Rate and a small down payment (5%) to get started on the new property. The numbers the first few years don't cash flow that well (damn PMI) so I'm currently letting that soak in and trying to model out what numbers make sense.

I also bought my first 2 unit property out in the West suburbs so have about 1.5yrs of experience as a "removed" landlord (property is about 45mins away from downtown). I'm happy to report it's currently a success from a cash flow perspective!