I have been watching the game from the benches for too long and I will start here by asking for advice on a business idea I have been thinking about to help jump start my journey. 

What bench marks did you use to determine you are treating it as a hobby.One of the primary differences between the two is that in business all decisions are made with only the bottom line in mind.

So an excavation company or a pot hole filling company?

Personally on my two long term buy and holds, I have a $300/door bench mark that I was aiming for.

I've seen countless FB discussions where some people (usually always young white people ironically) stirring this pot by saying things like how a black family simply cannot buy a home outside of the traditionally African American areas and especially places like Waukesha county, which is complete rubbish and I've seen first hand examples, not a whole lot but some, where it has worked out just fine.

I've had to pull a pot plant out of the front yard, etc, etc.  

I enjoy a big breakfast, pot of coffee, a little workout, and then I get on the computer and get organized to start my day and check for any new listings or e mails.  

That way, he'll get a lot more up front.If you don't have the credit or reserves to go to a bank, you could either negotiate the down-payment lower by sweetening the pot some other way, or get an investor to front you the remainder or the money you need (get a loan from them, make them an equity partner, etc.)

If it were me, I'd buy the note with contract of sale for no out of pocket cash to noteholder and push all possible risks onto them, using my skills to foreclose, clear title, capitalize, repair and prepaid for retail resale.To sweeten pot, offer listing to him if he's halfway competent agent (have my doubts). 

I know better than to think you're going to do this type of work and not put some of your own money in the pot.