New Investor moving to Chicago

[Lance Blight]

Hello everyone! I am a 20-year-old pilot who is currently living in Traverse City, MI, originally from Flint, MI. I'm about to finish college, and I'm looking to move to Chicago. Depending on which job I take out of school, that could be as soon as 3 months, or as much as a year and a half. My journey to BP started on Reddit. I'm an avid follower of financial independence blogs, which then brought me to real estate investing. My goal right in the next 5-7 years to have a multi-family home that I live in and rent part out, as well as a property located in a beach town that I can AirBnB and use as I please.

My first purchase will most likely be the multi-family home which I can then "house hack." I'm not a huge fan of roommates, especially people I don't know, but don't think I'd mind a multi-family home since I've had to deal with apartment/dorm living all of college and it isn't that bad. I'd love a home with a 1/1 or possibly 2/1 for me, and then another unit or two to rent.

I'm going to have roughly $25,000 for a down payment on an FHA or traditional mortgage, leaving about $10,000 left over for any major problems that come up. I'll keep that extra $10,000 for any problems, but ideally, the unit I'll be renting will be turnkey; renovations on mine are ok. What worries me though is that some of the price points just don't make sense. I know that some deals don't even make it to the MLS, but the rent prices just don't make sense compared to the purchase price.

This brings up my biggest question - Is it still house hacking if you have negative cash flow? I may very well may be $500 short of my mortgage each month, but that still seems very nice to me. $500 plus my share of utilities to live in Chicago? I know it isn't cash I'll see in my pocket, but that sounds like a solid investment, but I've got to be missing something. The ideal location for me would be within walkable distance to the Blue Line, anywhere between the Loop and O'hare, with a focus on Logan Square. I'm having trouble searching the forums here for relevant threads as I don't see a search bar, but I found one through google that seems to say it's doable. 

My goal isn't to really retire early at this point, just financial independence, but I'm sure that will change with time. I look forward to connecting with you all!