OR I could do a househack in Chicago near family, but I may risk slowing down my Bay Area business by not being as physically present, and I would have to leave daughter with family during the school year to come back to service the business which I'm not sure how I feel about.Ideas?

Look at the competition and see how this property compares physically as well as price and features.My opinion is that if you're an absentee owner with 200+ units, then you absolutely need a manager in place.

They are physically located behind the Ray Price Harley Davidson off of S.

My job is very stressful and drains me mentally and physically to the point where I have no energy for my 9 year old son.

Spending money at the casinos is not. 

Ultimately, I opted to not use their rent-payment processing service because I ultimately ended up renting to a more "old-school" tenant that wanted to give me physical checks.

However, I have twice so far hit a wall due to lenders being reluctant to offer financing or underwriters not wanting to underwrite the loan because of my physical location.

They'll conduct lease audits, contract reviews, physical inspections, resident interviews, etc., and send me back a report.

You need to allocate some portion of that to land value as you cannot depreciate land and only the physical structure. 

Recent market surveys indicate that about one-third of millennials will purchase a new home without physically viewing it first.