The city has been trying to decrease density in areas it wants gentrified for a long time. 

A good way to gain money for retirement, etc..

I believe in putting in the work—1,000 hours of research, testing, and learning—before offering advice, and I’m excited to tap into the collective wisdom of this community to refine my approach.Here’s where my head is at: I’m considering strategies like short-term rentals (Airbnb) for higher cash flow, long-term rentals for steady income, or even creative options like house hacking or partnerships to stretch the funds further.

Lots of really good seafood and live music. 

If you went over budget , there is a good chance you either over inproved the property  or you paid too much from the start . 

Good luck with the project!

Some exceptions can be made but the only real way around it would be to get a solid cosigner for the loan with a good W2.

Sounds good - I hope it works out! 

I would recommend you begin researching Chicago based meetups as there are a bunch of really good ones.

What im hoping to gain from this group is knowledge i cant find anywhere else, i hope to meet people that i can help and people that can help me, I hope i can form good friendships on here, and i hope to find my first rental.