Eric R - $1,800/month

I am a successful self employed businessman/professional for 21+ years. I have also have an extra source of income, guaranteed income which I will explain later. I have never been married but I have an absolutely adorable 7 year old daughter. I have been in 3 long term relationships one of which I was engaged for a short time, but right now I had to move out of the city for a couple reasons back in October and really miss it. I live in the suburbs with my mother temporarily until I can get her into an assisted living place. I am originally from Hinsdale and came from money, family money, but decided to make money and a life for myself on my own steam. I used to live in the Lakeview area and before that on the Southside near Midway airport. In the meantime, I'm looking for something simple and comfortable. So if I sound like a viable roommate please respond.
Thanks
Oh, please don't hesitate to ask questions