I'm at the point where I realize that my body can't handle this kind of labor (50-80 hrs wk) for another twenty years and have always had an interest in real estate.

We also have a newborn and would like to remain in our current home with her at least for the next few years.I'm willing to get creative, willing to get my hands dirty (as in demo/construction, not burying bodies...). 

Dee Jay Chicago has quite a few issues and property tax increases seem to be one of their favorite ways to solve them.In a city like that I would also be afraid of regulatory hindrances like rent control and the city just not being landlord friendly in general.

Taking into account climate change, the regulatory environment and future growth (population and real estate valuations), cities like Charlotte, Nashville, Chattanooga, Atlanta, Birmingham, etc etc should win handily against costal cities or the rust belt.Ultimately the best city to invest is the city you can invest in first and the most sustainably.  

Where we dedicated all our time on learning about the marijuana county ordinances, zoning, and other applicable regulatory decisions.

@Tyler Bodi 40216 is a big area and depending on where you are at in the 40216 this may be a fair deal or a not so good deal.

You give them your Arm, they devour your entire body.  

standing over my dads casket looking down at his body ,realizing that someday that will be me ..dying broke without enough money in my savings to even cover my own funeral .

If you can find a job requires a warm body, but let's you work on your own stuff from a computer, you're set!

However if you go outside of city limits then the county has more lax requirements and they are subjective about what is an MHP versus what is not - sometimes it's 4 homes, sometimes more.Most water wells can support multiple homes, it's more about the treatment equipment sizing (e.g. chlorinators, filtration systems) and ability to keep up with demand, and also regulatory requirements of water testing once you have 15+ homes - it becomes an EPA thing instead of your state DEQ.