New to House Hacking - Chicago IL (north side)

[Morgan Van Ness]

For the last year, I've been browsing Chicago real estate and working hard to save up for a 20% down payment.  Just two weeks ago I was introduced to the concept of house hacking and absolutely love the idea.  As a result, I've spent the last two weeks reading the guides and listening to all of the podcasts about house hacking and finally have a basic understanding of the underlying math and the concepts.  I still have no idea what to look for in an actual property, but I'm excited to finally start understanding what the terms mean and how to do the calculations.

I've rented all over the north side for the past twelve years, never staying in one unit for longer than two years.  Did two tours in Old Town, twice in Lincoln Park, spent some time in Lakeview, and am currently in Roscoe Village.  Work full time in sales and am a remote employee.

My landlord is debating whether or not to put my unit up for sale this spring, so the time has come for me to start looking into what is next.  Ideally I'll re-sign for a third year (whoa) and tackle this in the spring when I have another year's savings under my belt, but I am prepared to move quickly if need be, much to the chagrin of my fiance who wants me to focus more on wedding planning.

Ultimately, the goal is to go slow and see how we take to the concept of landlording.  The first goal is to find a solid house-hack on the north side, ideally near the brown line.  We don't really have any ambitions of living for free at this point (obviously aren't opposed to it, but would rather stay realistic), but love the concept of having some support tackling a mortgage.  When we move out, we'd like it to be cash flow positive so we can start working on the next project.

I'm looking forward to learning from everyone here and getting this process started.  Other passions include skiing, BBQ, eating/drinking (craft beer/scotch consume a lot of my energies), and generally being near, on, or in water.

Cheers

-Morgan