I'm a local investor, flipper, and property management company owner.  

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.

I'd rather invest with the local 26 year old who lives in their second house-hack, drives their 10 year old car, and is raising their first small apartment syndication that they will self-manage, putting their own money into the deal, than some 45-year old guru who's secret sauce turned out to be their ability to charm on TikTok, but really, their approach to deals ended up being the "secret" to transforming $300M in real estate into $215M between 2021 and 2025.  

I also did a local renovation in 2022 bringing it up code.

@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's the zoning on the property and do you have a relationship or contact with the local rep? 

Send them a written notice of non-renewal, following your local laws about how much notice you need to give.

Property taxes will likely be reassessed based on the transfer value, so confirm local rules to anticipate potential increases.If you hold the property for at least one year, you can use the equity as collateral for a construction loan, aligning with your long-term financing plans.

My guess is that the institutional big banks would have a problem with it, while the smaller local banks and non-bank lenders probably wouldn't care as much. 

Are you considering expanding locally or branching out to other areas?