If possible, consulting a local real estate agent or financial advisor can provide personalized advice based on the specific market conditions in Chicago.

I am going to message you my personal point of contact there :). 

It's a great place to network and connect with others in person.

These technologies are not just passing trends; they are the vanguard of a new era, swiftly outpacing the conventional workforce.The Rise of AI and Disruption ToolsThe real estate industry, once reliant on personal connections and local knowledge, is now being reshaped by AI.

For any new acquisitions though you’ll likely want to buy in a new LLC just to create some separation between your personal liability and your rental properties. 

Personally, it's no one's business how many doors you have unless you're seeking a partnership, loan, etc.

Property that generates rent and that the owner has personal use of (your family member) can qualify as investment for a 1031 exchange easily enough. 

Also, make sure your property is in a LLC and not personally owned for any potential lawsuits.

As that will at least help folks that you reach out to know that you are a real person, with a picture and professional bio.

We value the flexibility of using it for personal purposes when needed, but maximizing its potential for income was the primary reason for its construction.I am seeking input and feedback from the group regarding our current situation.Thanks!