An investor at my local meetup suggested contacting sellers on Craigslist by asking, "Would you consider a rent-to-own solution for your home?" 

Hired someone local for maintenanceAny other suggestions to get off on the right foot?

Add it to your list now.As for suggestions as what to do.

He's looking to move in the spring (unless he's motivated otherwise) and I'm sure he'd be interested in a less complicated exchange, with less effort and outlay of cash for him to "prep for sale".Help and suggestions would be appreciated. 

@Charles Mitchell I suggest going to AAA and getting a map of the city.

@April RobbinsWhat you're suggesting is the "repeat"  part of BRRRR.

@Chuck KautzHey Chuck,I like your idea of getting your daughter involved.As a father of 2 kids that went to college I think this is a great time to expose your child to what the whole process involves from purchase to rehab to managing this property.Your child will get so much real world experience out of the process I hate to say but this exercise my have more of an impact on her life then the BA has!

Will this be an exercise in futility?

. :-)You can show time all around and see what they suggest, but it doesn't give you a chance to build rapport with all three there at the same time.

If you try to "look the other way" and quietly allow more than the max number and neighbors complain to the city you can be fined, dragged into court, and the city can even shut your power off.In a nutshell, unless you have family or some other strong connection to this city, I would strongly suggest anywhere but here.