For example, a buyer putting 20% down on a $500k home would pay around $500k in interest over the 30-year life of a typical mortgage at a rate around 6.5%.

Hey @Mordechai Chaimovitz - It sounds like you are talking about Chicago's NW side because there are definitely tons of areas in Chicago where a 2 flat can cashflow well.I know for me buying on the nw side was critical to my personal well-being and life happiness. 

I would pick a market area you like and start doing a bunch of deep dive deal analysis, but from a rental and not a life style standpoint.  

Instead, investing should be a means to taking care of our needs and improving our life style.

I wanted to create an STR experience and bring my bold ideas to life.

I've been a real estate investor my entire life, doing my first deal as a senior in high school ($5,000 mobile home).

My mom is nearing the end of her life and has left me and my two brothers her condo in Hawaii.

We both run our own businesses but we feel that real estate will help make sure we both maintain our life plans of not needed to work as much any more.

Explore my personal favorites, Set For Life by Scott Trench or The Total Money Makeover by Dave Ramsey, for invaluable financial insights.3.

When you move out you begin to experience POSITIVE CASH FLOW in which your tenants help you buy the property.....where eventually you own it out right, and now it becomes like a pension..........Predictable and Sustainable income for life.