Dennis' dad and I actually tripped over something similar back in Chandler.. we learned to tap into city planning websites and even call the permit offices directly to get a real sense of their backlogs.

Here's the City link for you to reference. https://www.chicago.gov/city/en/depts/doh/provdrs/homeowners...1) ADU regulations specifically exclude Short-Term Rentals so don't do it if the intention is to short-term rental. 2) The ceiling height oh 6'10" is almost guaranteed to trigger digging a basement if you want to formalize as an ADU unit, especially if that height is further reduced by pipes or HVAC. 3)Ingress/egress is an issue for renting, as is that any bedroom also will need two (ie operable window/doorway).

It depends on what exactly you are referring to with gap funding.

You'll likely want someone that can handle A to Z with marketing, pricing, cleaning, maintanence, decor, websites, reviews etc.

Save related articles to the cloud for reference. 2. 

How to Track Regulatory ChangesStaying up-to-date might seem daunting, but the right strategies and resources make it manageable.Key Resources:Local Government Websites: These often publish updates to zoning, rental, and housing codes.Real Estate Associations: Organizations like the National Association of Realtors (NAR) or local landlord associations offer regular updates and seminars.Newsletters and Blogs: Subscribe to reputable legal or real estate blogs for insights into upcoming changes.Professional Advisors: Build relationships with real estate attorneys and property management professionals who can provide guidance tailored to your market.Pro Tip: Set up Google Alerts for terms like “rental law changes” or “landlord regulations” in your area to receive real-time updates.3.

The tax benefits refer to the tax deductions from mortgage interest and property tax.The returns mainly rely on appreciation, and the cash flow only improves in the last few years, also depending on securing the 5% refinance rate.I've learned a lot from this forum, but as I start to operate on my own, I'm still not completely confident.

With setting up LLCs would someone go to their Secretary of State website and do this?

If you would like a few references to property management companies within the city that are local I have a few recommendations. 

The homes that you used to determine your ARV are a good reference point.