I own a construction company and would manage them and manage maintenance myself, and likely even rent a unit to myself to keep it simple (I’ve been a resident manager before too).

Turning a single-family home into a room-by-room rental strategy really paid off, especially in a neighborhood like Portage Park where whole apartments typically rent for less.The demand for month-to-month flexibility is growing, especially in cities like Chicago, where people might need shorter-term housing due to job relocations, school, or other temporary situations.

They like the idea of owning this property as a rental and then eventually having it for a family member to retire in since it is one story and in eye shot of their current home. 

I’m also passionate about financial independence and building long-term wealth through real estate.Looking forward to connecting with like-minded people, learning from your experiences, and contributing to the community.

They say short-term rentals like Airbnb and VRBO are NOT allowed in the city of Morrison.

Would like to get some feedback about your experiences with them as I've heard nothing but good things. 

I hear people having rental properties older than mine like 1900 still cash flowing and happy.

I feel like this deal pencils at $365-375k but need to add a bathroom, redo kitchen and existing bathroom, close in garage port for more sqft, + cosmetics and new appliances.

and I think a HELOC doesn't feel like debt the same way as other types of payments."

I would not trust AI with anything really important, like writing legal documents or designing a new house.