As for the rest, I've started reaching out to past people I've crossed paths with in the business. 

I have a go-to I use for that.Then the rest should be a handyman that you find.

I don't think they will be lower than they are right now for the rest of our lifetime.

Owner would like a downpayment of 400,000-500,000 and will finance the rest at rate lower than the banks could provide. most likely over the course of 15-20 years.

So they go sign a lease next door.Now you could be in situation where you have to actually lower your rent to come to market with the rest of the competition.This is how I would see it playing out in the Cincinnati and Dayton markets where we do property management. 

How do they expect me to live here for the rest of my life?

Could put 40 - 50% down to improve cash flow, keep the rest in the Market

If I can do that, it'll make enough money the rest of the year to cover expenses and spit off some profit to make it worth the hassle.

Development site visits give me 6–9 hrs/week, the rest from active management across Auburn, Kent, the bar property, and the basement rental.Would love feedback if I’m on the right track and if there are blind spots I should tighten up.

From my conversations with him, he gets about 2 weeks where he works 60-80 hour weeks doing the turnovers in June and under 5 hours a week the rest of the time.