So deciding which homes are "better" is something of a complex formula.So I recommend South Side and Friendship based on modern patterns of urban renewal along with some attributes of solid building stock that would offer value to an investor.

Contractors tend to make spaces too small and non functional to increase profit and or lack design knowledge.I would build modern style...

Welcome to the Society-Family Joshua.  

So having modern electric/plumbing helps a lot.

Many people could care less if you ask and will talk openly about a disability but unfortunately our politically correct society is fixated on the lowest common denominator so this is unfortunately not possible.I much preferred the age of ignorance when people could actually communicate openly. 

I also vote no-go.If everything goes perfectly, this deal on paper works, but we live in a world with vacancy, improvements, modernization, property management, and surprise issues (roof needing repair, needing a plumber, fixing the garage door,..)If your goal is to buy an investment, I can help you find better deals in the Twin Cities.if your goal is to buy something close to where you personally live at this point in time, you already have the answer.Again, I vote no-go.

Look for markets that have growing popluations, jobs, incomes and diverse, modern economies.

Indianapolis is a great market not just because it cash flows well but it has strong economic/demographic trends such as a growing population, growing jobs, a modern economy with a diverse employment base.

In the current market, I would focus on Tacoma which has some really awesome neighborhoods with great old houses (I don't care for modern ~post 1940's construction) at 1/2 the price of similar homes in Seattle.

Using modern windows in a house that old never works out well.