23 years old, looking to buy my first property in 2 years

[Carl Braxton II]

Hi All

I am 23 years old, currently living in Tallahassee, FL, but I am from Chicago IL.  I have renewed my lease for another year, so I will be in Florida until 2027.  Over this span of time, I want to position myself to buy a property in Chicago.  By 2027 I will have 2 years of work history at the same job, and I have just opened a secured credit card. I will also note that I am looking to house-hack.

What kind of properties would you recommend me to start looking at (preferably regardless of location)?  

Any areas in Chicago I should focus on, or stay away from?

Should I be concerned with purchasing my first property via an LLC?

Through my continued research, I will better understand what questions to ask, so please give grace

With Gratitude,
Carl Jr.

[Aaron Zimmerman]

Great choice with looking to house hack and in Chicago. It's one of the best markets to do this since 25% of our inventory is 2-4 units. I favor the northside neighborhoods because that's where I'm personally closest too plus historically they've appreciated at faster rates than many other neighborhoods in the city.

I'd first focus on where you want to live first and then go from there. If you're trying to live in a place like River north or streeterville, probably not super affordable. However, if you're okay living in more north neighborhoods (edgewater, rogers park) or northwest neighborhoods like Irving park, Belmont cragin, Jefferson park, portage park, you may have more success