That being said, I scrapped the idea and bought another rental property.One hack to consider, a colleague of mine finished a third floor, made the third floor the living room and kitchen and the second floor the two bedrooms because that scenario avoided the need for a second means of egress.

If you go the single family home route, I would find a house with 4-5 bedrooms so you can live in one, rent the other 3-4 via house hacking.

We don't like SF houses that have been hacked up into apartments, only buildings built for multi. 

Welcome to Chicago, and congrats on starting your journey into house-hacking!

We have been pondering the idea of house hacking. 

Many find it’s entirely possible to balance both, especially if you start with smaller projects, like single-family rentals or "house hacking" (where you live in one unit and rent out others).

And the first property was a house hack where I rented out bedrooms to cover mortgage, while living there for basically free. 

I'm not sure what the path to begin looks like, but I've been researching about different approaches, specifically multi family properties and House hacking.

Hello everyone,I'm looking for my first small MFH to house hack in.

Quote from @Jose Quinones: Quote from @Jonathan Greene: If you are in the market for a house hack, wouldn't you intend on living there and using the owner-occupied?