When I say manage I don't necessarily mean managing the property yourself, but you could hire a management company, you could put a team of people together to assist you with investing (agent, contractor etc).

@Charlie Hyatt Roof, HVAC, plumbing, and electrical because we are adding electric heat to the 3rd floor.

And where should I find a contractor?

We've even lined up friends who are contractors to help us for the rehab.

I'd worry about the most expensive things in an inspection/walk-though, foundation, roof, windows, HVAC, electrical system and plumbing. 

Even going with private money rolled to new permanent financing would open the door to many more properties and more options for contractors and scope  and grade of improvements.

Michael Guzik do a walk through the property with a contractor to get an idea on rehab numbers.

So there is no easy way to tie a W/D into the existing plumbing, so you will need to add a new drain stack which can be $10k-$20k depending on location, plus the cost of the W/D - You will not get that back in rents for many years. 

He is an excellent General Contractor in Chicago. 

Talk to the contractors who did the work if you can.