Chicago Real Estate Independent Contractor

[Brandon Gates]

Bigger pockets community,

Hope that you guys are off to a phenomenal start to your weeks. I have been in a pickle over the last few months on how I want to approach my next rental project. A little rundown on my current situation. I recently purchased my first investment property about 5 months ago in McKinnley Park that is a duplex that I am house hacking. The househack is going great and it's making me want to get another property under my belt. Right after I purchased the property I became a full-time real estate agent under 1099. My goal is to buy another investment property within the next 6-9 months but am having trouble figuring out what the best plan is for me due to not being able to get approved without 2 years of stable income. My first thought is to bring in a co-signer to invest in a single-family property or condo that needs a little TLC. My other thought is that I just continue to live in the property that I am now to reap the tax benefits from living in the property for two of the first 5 years to avoid paying capital gains tax. I am curious to hear some more experienced investors' insight on what they think would be best for my situation? A few questions that I have been thinking about

Are condos good investments in the city of Chicago?

Should I stay at my property now to reap all tax benefits as opposed to buying again?

Any other ideas on creative ideas on ways to finance a property?

Looking forward to hearing all of your insight!