I am wondering if this area has scope for home appreciation in the future and whether houses are rented easily? 

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.  

My clients bought one that was four bedrooms with a den (just needs a closet) and a loft area (which could easily be converted). 

Even smaller rehabs can easily take 90–120 days from purchase to resale when you factor in inspections, permits, contractor schedules, and unexpected issues.

It also gives them a front row seat on delayed gratification, long term thinking, investing, and tax planning.

I think you have a good idea to have a big hangout area that also has functional uses like laundry, seating, etc. 

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

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.

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

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