Not sure your situation financially but even your $100,000 HELOC is going to probably run you $12,000 additional each year in expense that you've got to factor in.

BiggerPockets is full of resources designed to help you along your journey, whether you are just getting started or a seasoned investor.

@Jennie Berger gave you the whole kit & caboodle on Chicago zoning so I don't have a ton to ad, however, I'd highly encourage you to engage an architect like @Samuel Pavlovcik or @Prashanth Mahakali, both are awesome local Chicago resources.

What are the financial metrics i should be asking for?

However, our goal is to help 100k investors obtain financial freedom - hence the reasons why we provide many videos, podcasts, programs, and services to help with this journey.Unfortunately, we cannot promise that every deal we help you get under contract will close.

In efforts to get more experience with IOS, we are seeking a financial partner that potentially has experience with this asset class. 

Great tools that get updated regularly.I am on the lending side of things and would be happy to hop on a call with you anytime to discuss financial strategies and help answer any questions you may have about nearly any loan product available to help you on your journey, even if they are not products my capital partners offer.We are all here to help you learn and grow.

You could see an attorney or even better talk about it with your financial planner many have legal tech now that makes it essentially frictionless to get your estate work done and keep it updated.  

Quote from @Danth Aman: Quote from @Victor Patel: I don't see a problem with this as he has disclosed his financial interest in the property and him being a licensed agent. 

It means your house might be your biggest financial asset — and it could open up some exciting opportunities for your future.