The duration of the project will drive how you structure the financing.  

We try to fly down every couple months and just drive around to get to know the neighborhoods.

With the market where it's at, with so many people overpaying and thus driving prices up and making deals assets less lucrative, this structure allows deals to still be attractive for upside investors while providing a nice safe (in some cases, not all deals are safe/good) investment for those who are looking for capital preservation over growth.

For a few here or there I would take a drive to your local hardward stores, Lowes, Home Depot, and see where the best prices are. 

I only buy RE within a 2-3 hours drive of where I live because that what I can manage and also can find great deals. 

For those familiar with the area it's right off of outer drive and southfield fwy. 

Then I took some action by driving for dollars I sent out hand written letters and took phone calls (some very angry) after 7 letters to each homeowner (over a few months) I sent an actual contract offer to every person (interested or not).

Drive deals on BP and in real life and your portfolio will continue to grow!

It's a healthy and diverse economy with projected growth, but its also a city surrounded by open build-able land, which means it doesn't have the same kind of condensed urban core, where scarcity of land drives rapid appreciation like in other major cities. 

Well, I'm going to guess you will find more affordable starter-investments in Kenosha than you will in Chicagoland or, do you just prefer to drive north instead of south!!!