If the unit does not comply with local codes (like proper egress, zoning approvals, safety standards, etc), it cannot be legally rented regardless of how it’s marketed.The safest course of action forward, would be to bring the unit up to compliance with chicago's zoning/ building codes before attempting to rent or advertise it. 

But we just can’t pull the trigger on anything.

I checked out ab968, looks like pre / foreclosures might be a good way to go if I can find them. thanks everyone for the responses, really great info. im actually starting to see more deals on properties in need of renovation so I’m hopeful I’ll be able to find some good flips when I’m ready to pull the trigger  

This could trigger the FHA 100 mile rule however with a few exemptions.Indeed, FHA allows you to put 3.5% down payment to invest in 1-4 units.

I've considered putting solar panels on my investment properties, however, I have not pulled the trigger yet.

There will be a consultation and assessment to determine your business goals, strategies, etc.Research to identify the grants that are most aligned with your goals and strategies.Preparation of documents using a checklist to simplify the process.Application submission.Follow up with you, the client for clear compliance and reporting expectations once a grant has been awarded to you.Here are a few resources for accessing grant funding:Grants.govUSA.gov/GrantsNational Institute of HealthSmall Business Administration - GrantsHave you utilized grants in your real estate portfolio?

S-Corp) to minimize taxes while maintaining compliance in Indiana and California?

Quote from @Jon Taylor: @Pete Harper - Section 721 of the Internal Revenue Code allows an investor to exchange property held for investment or business purposes for shares in a Real Estate Investment Trust (REIT) without triggering a taxable event.

The main reason I'm asking this, is to understand how much cash I need to save up in reserves before pulling the trigger on a deal like this?

This allows you to invest in real estate without triggering the 10% early withdrawal penalty or income taxes, and the gains can grow tax-deferred (or tax-free in a Roth IRA).