I live in Portland  Maine , I am new to real estate investing and looking to connect with any local investor.. thank you.

@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.

Reaching out to local agents?

I am new to real estate investing and looking to connect with any local investor.

Focus on smaller single-family homes, condos with low HOA fees, or multi-family properties in these regions, and build a reliable local team of agents, property managers, and other professionals to ensure a smooth investing experience.

I am a local investor, lets connect, Michael!

Ensure the property’s price aligns with market trends, and work with a local realtor to help with due diligence and negotiation.Good luck!

In my experience, success in D-class areas almost always requires being local, extremely hands-on, and self-managing.

They often have different vendors introduce themselves so you can build your team and they often have a local member do a case study on one of their properties to share the ins, outs, ups, and downs of the investment.

They are usually looking at C or D properties that local agents tell them will “cash flow“ They usually don’t cash flow because of high maintenance and vacancy.