For a new investor I'd say take this time (at the top of a market cycle) to establish relationships with a team that can help you when those deals are more plentiful.

Once his feet are back on the ground you can establish a true value.

When respect is no longer being served, leave the table.

Establish LLC for flipping business to save myself from personal financial liability or lawsuits3.

I have the opportunity to House Hack another 4-Plex in my home down (which I'm also pursuing) and "wholetail" with my father, both of which wouldn't consume all I have.I respect this man's time, and I don't want to leave him hanging. 

The numbers look great on this property minus the rental situation, with a $400 cash flow with generous vacancy and maintenance % estimates of 10% and 30% respectively. 

Would it be better to 1031 exchange into multiple turnkey single family homes that are already established and can cash flow within a month to two months?

I would largely consider JC to be worth considering and checking out, depending on the condition of the building in question, but I imagine it's going to take a few more years before it becomes and established area like the west side is.

From my perspective, you are doing everything right and handling things in a professional and respectable manner.

I do know that anyone looking to do parking garage developments in city centers will be out of luck when self-driving becomes established.