Getting started in Chicago

[Chris Lee]

Hi - excited to join the BiggerPockets community and learn from everyone here.

Would love to have your thoughts/feedback as I am looking to get started with a first investment property. With a long-term goal of buy & hold multiple properties with rental income, here are the options I am thinking about:

1. Ideally, I would like to buy a 2/3 flat in Chicago - North Center, Roscoe Village, Lincoln Square, Ravenswood, and rent 1 or 2 units and keep 1 unit for when I visit. I no longer live in Chicago but am from there and visit often. I’m just getting started and 2/3 flats are pricey in those neighborhoods, so there’s that.

2. Buy a 2/3 flat at a lower cost in other areas of the city (open to suggestions) and rent all units. I’m assuming I could possibly put down the same amount and buy up to 2 buildings for close to the same cost as option 1.

3. Buy single family and rent instead. Open to area suggestions as well.

4. Flip, but this is least likely as I don’t have a team in place yet.

Any thoughts would be appreciated. Thanks!

[Aaron Zimmerman]

I second @Jonathan Klemm's question. Why not invest in Minneapolis and perhaps do the house hacking strategy? Your dollar will go further there. Should you need any connections, I have a friend that recently completed his house hack in Minneapolis that would be a wealth of knowledge. He bought a fixer upper and it has very strong cash flow. I'm from Minneapolis - now living in Chicago so I'm a bit partial to my hometown! Absolutely love Chicago though but a bit tougher if you're looking to go remote. I also think Minnesota has a friendlier business climate as well.