House Hacking vs SFH Investing - Chicago Suburbs

[Christian Bernhagen]

Hello all!

I have a few quick questions in terms of house hacking and your thoughts on where I should go with this route specifically the Chicago southwestern suburbs in today's extremely hot market. I graduated last May and work a full-time job as a commercial property tax consultant with about $20,000 in savings and counting. The past several months I have gotten several properties under contract in the Elmwood Park area and surrounding areas, but all have fallen through due to FHA financing (owner did not accept this financing route, buildings had too many repairs needed to pass FHA inspection) or the numbers simply did not work in the end. Do you suggest I keep saving to increase my reserves to find a better opportunity in an area similar to Elmwood Park / Wheaton (currently living at home with parents, but plan on moving out by end of March. I want to find a similar (B+ to B-) area). The price points for areas such as this one are well beyond my financing limit for the numbers to work out and cover my mortgage (mainly looking at duplexes) in today's market. On the other hand, do you suggest I start with single family home investing and renting a cheap apartment closer to my downtown office in the meantime? I do not plan on house hacking a single family home.

Thank you!