He’d then work on;y with buyers whose criteria was to buy “great” deals; who had cash ready or financing easily lined up, and who we’d motivate to move fast.  

First is you need a way to eliminate the current mortgage to get her name off the loan, this would likely be easiest with a refi.

But the biggest problem is newbie and wanna be investors bidding up the price to levels that eliminate profitability.   

I think you could easily save $50,000 a year doing this and maybe more. 

;t=94s I have no experience with this, but with anything my first thought is: How can I add more value.Although I personally am not a fan of solar, it might make more sense in areas like you mentioned to mitigate or even eliminate long-term energy costs.Rain harvesting systems too.

Is the PM company easily available when tenants or owners have questions?

Is a trip to the area required or should I be able to switch Property Managers from afar fairly easily?

A good PM should easily outperform a self-manager.

That money could instead end up in my pocket, opening up a lot more space for cash flow, and allowing me to put more money into more investments.I am going to hold the property for 10-15 years anyway, and unless I'm really bad at homework, the property is going to double in value during that time, allowing me to easily pay off the loan.

It's not a matter of luck but having an understanding of the local laws, neighborhoods, and connecting with the right people (building your team) to leverage their expertise.Since you currently live in Illinois, and unless you work remotely & can easily relocate, it's probably best to keep searching for a decent property to house hack to take advantage of owner occupant financing.