@Shaun Peterson  I'd have to agree to disagree about your sentiment that most dont see the value in Delano - As far as where your lot is situated you may need to sit on it 20 plus years - the immediate area and surrounding blocks are run of the mill basic SMALL entry level houses.   

If i am new player .. i would do the following:1) Save up cash that i can spent within minutes 2) Become master analyzer of a given area so that I can analyze the deal within minutes  and know the buy/sell characteristic of every single block on that neighborhood 3) Network heavily with wholesellers (only individuals...

Josiah,The property is in the Ellet area a few blocks from the high school.

I feel like I have hit a point of information overload and need some help with steps / questions to push past this road block and take action!

It's also possible that he had a conversation with you about "Real estate professional" status which helps to unlock deductions blocked by high income.

The plan would be to paint it all a single color. 

It’s a block away from million dollar homes and very sought out neighborhood.

It was very block by block price wise with Zillow which for me doesn't paint an accurate picture. 

Talk to them about your deals.You can find rental properties on just about every block in the city.If you want to find ones for sale to purchase, they are almost all listed on the MLS.

I have included maps of all three places and their block level location grades, This should give you an idea of where to start looking.I would also give this a read if you haven't come across the location grade paradigm in your research yet:https://www.biggerpockets.com/blog/2015/12/09/class-a-b-c-d-real-estate/