If you are very conservative purchase a fixer upper so you can force equity and hopefully have a low enough payment so that you can LTR the property or even sell for profit should the STR avenue not work. 

I own a 200 year old house that has a very low cost of repairs and maintenance over the 4 years I've owned it.

I haven't filed a claim all these years but insurance is for the what-if and to be used for the high-ticker items, but chances of damages exceeding the 5% is low.  

Once complete, refinance into a low or no seasoning DSCR loan.

I made a low offer and it was accepted.

Some of it is luck or taking advantage of opportunities (eg low interest rates). 

I have purchased the following books:ABCs of Buying Rental Property The ABCs of Property Management The ABCs of Real Estate Investing The Advanced Guide to Real Estate InvestingThe Book on Investing in Real Estate with No (and Low) Money DownWhat order do you recommend reading them in?

I know the area like the back of my hand and believe Indiana has tons of upside to invest in.I came from a low-middle-class family of teachers.

Section 8 is best used as a risk mitigation tool for properties in super low income, high crime areas.

I would search for a property that has a low interest rate Fha or VA loan.