@Joshua Coleman- Hi, I used Real Estate School of Illinois, which I am not sure will be of much use to you. 

Looking for recommendations of a simple book or straight forward (short) video that explains the benefits of real estate investing to a teenager.

Find a market you like with a good future (strong schools, job market, low crime).Learn how to analyze property for good cash flow.Get your finances in order with no debt, a good budget, a personal emergency fund, enough money for the down payment, and a reserve in case anything goes wrong with the rental in the first 6-12 months.Buy.Immediately start educating yourself on how to manage problems (application screening, late rent, unauthorized pets/people, etc.) and saving for the next investment.Here's a guide that describes what good cash flow looks like and how to analyze a property.https://www.biggerpockets.com/...

It is an older home built in 1938, but the place is in decent shape, is furnished and designed old-school but could be very easy to make look decent with some cosmetic additions/changes around the house.

I'm new here, please feel free to school me on any incorrect assumptions I may be making. 

My family is super old-school and don't want anything to do with something like real estate.

I am looking at school districts, city rent control policies, annual incomes, neighborhood class, etc. 

To get technical, my girlfriend (now wife) was the sole purchaser as I just graduated from law school so my salary history (or lack thereof) dinged us on rates.

This is not a typical scenario happy warm house/brag about being homeowners this is strictly business and to give us a roof over our head as we transition in life (I work a relatively higher paying job that may not be around forever; she is in nursing school).

I'm looking at a property near Boston for $70k, decent school district, 5 minute walk from the train station (15 mins to the city), and median selling price in the area is well above current asking price (~$400K).