How crazy is my action plan?

[Greg Fuente]

I'm new to the forums although I've been listening to the podcast for a while. Due to a legal settlement, I have some capital to invest and I need some help/advice formulating a plan. At this point, my goal of $20,000/month passive income just seems crazy, but here it goes...

I am a 40-something California resident who spent time in the Midwest region during grad school. I'm looking to invest in single and multi-family rentals in Milwaukee, Chicago and Indianapolis areas. My plan is to put 20% down on 15-year mortgages for properties yielding ~$400/month profit. I am starting out with $1 million capital investment and looking to build separate management teams for each area.

Any advice, warnings, questions, and just general information would be greatly appreciated. I am looking to gather as much information as possible before taking the plunge. Particularly, I'm interested in ways to work around mortgage quantity limitations.