Condo Rentals in Chicago

[Michael Moskos]

Hello fellow BiggerPockets investors and members. I am a 23 years old, recentcollege graduate (Accounting) with little debt. I have been passionate about Real Estate for the last 2 years of my college career, and can not stop educating myself. The minute I obtained a job I began aggressively seeking a deal. Any deal whether it be a student rental, wholesale (calling distressed FSBO sellers), single and multi-family homes. The problem is I have spent 100's of hours networking and making phone calls to find deals, but have struggled with multi-family (primary focus) in the Chicago-land suburbs (do not meet my criteria).

I realized I need to refine my approach. I used to be the most anti-condo friendly person out there. Although, after briefly educating myself, I believe a methodical and careful approach can lead to a strong condo investment. I am looking for some advice and education on the Condo market in chicago-land area. For example, because my capital is currently low, I cannot fund a 20% investment downpayment. For the time being, I am looking to by a strategic investment (condo at a discounted price in a good market) and potentially AirBNB it on weekends and even some weekenights. I am wondering if anyone has advice or experience renting condo's with AirBNB? I know there is associated risk with HOA guidelines (relative to the HOA). I am wondering if anyone has had success (positive cash flow) doing this? I love any and all advice and am 100% open to learning. I really apprecite you all taking the time to read my lengthy post, and look forward to networking with you on BP!