I also would drive the alleys to see what types of cars were parking behind the buildings.  

Think of it like a car: Learning is RPM, Doing is MPH.

Two bedroom, three car garage, large lot, etc.What locations are likely to do well today and into the foreseeable future.What rent range best matches the pool of tenants most likely to be good, long term tenants?

Your buyer is going to be a young millennial family who is priced out of Fountain Square, Bates Hendricks, Herron Morton, etc.Spend the extra $25,000 on building a detached 2 car garage with alley access.

I was just thinking about how I'm tired of living so far below my means, strictly budgeting, and driving a crappy but "reliable" car.

It's on a slightly busy road with lots of cars going by and lots of witnesses.

You can use that for repairs or a new car.

Hey guys, Myself and a few friends are looking at getting our first buy and hold rental property, the three of us are just out of college based in Wisconsin and we are pretty open to where we should buy our first property, so far we have looked at Chicago because it is so close but it seems like most good deals in Chicago are pretty obscure, that being said we could definitely use any advice we can get regarding where to look, how to secure funding, and how to create value in our first rental when we purchase it, pretty much any advice you can give to a aspiring investor would probably help us.

Rent a car for $200.

I don't mind agreeing to her rates and everything but don't really want to sign some obscure legal document.