You need a siteplan that you can present to the city.

I started out researching my market by cycling the city and getting in shape.

Verifying last 2 years of rental history and income extremely important to find the “best of the worst”.Make sure you understand the Class of properties you are looking at and the corresponding results to expect.The City of Detroit has 183 Neighborhoods we’ve analyzed.DM us if you’d like to discuss this logical approach in greater detail!

Rehab is nice so I don't think that will be a concern, this is also off street parking so ones with garage will be favored more if you are priced the same. 

Here's the link for your city https://www.furnishedfinder.com/stats?

The city of Cairo and Alexander County as a whole are in a very depressed economic situation.

Michigan and any other reasonable Midwest city.

I would like to think in a way that investment in general, and the real estate investment, start with a solid economic reason - "Why do you Invest, where you invested".To elaborate on below - Vegas is a great example where no real economic driver exists and when you invest there, you should be aware that is a highly volatile market (side note: i both 2 properties there in 2011 and 2012 and i sold both this year) and you should pay an extra attention and be prepare to reposition capital.It's clear, if you invest in Vegas or Orlando (just 2x entertainment cities) you will expect ups and downs and you need to position yourself with extra reserves and extra caution if you are planning to stay in these market for long term. 

The setback requirements to build in my county require 80' minimum wide street frontage per this neighborhood zoning.

This reminds me of the story of a wall-street banker convincing a fisherman who already has time for his friends / family to instead scale his fisherman business(get employees, integrate, then sell the business) all of which will lead him to be able to spend time with his friends and family.It already sounds like you have a great life - spending time wth family and in great health.Having additional money doesn't sounds like it would improve your life that much.