I deal with it on a state level at my 9-5 and it drives me insane. 

Make sure to verify all information and ideally speak with an experienced investor who acquires in the respective state before proceeding. 

Ideally I would want him to drive by the home, snap some pictures of outside/inside problem areas to give me ANY idea of repairs expected before an offer is put it.

@Steve Onay Texas will likely be a bit more landlord friendly than Chicago, but as you referenced, the building stock in Chicago is just ideal for house hacking.

Hey @Alex Jacobs, I'd start by finding a solid investor friendly agent in your local area; definitely meet with a few of them, but ideally you will find someone who has a decent network that can connect you with resources such as a solid lender.

Ideally what I would want to do is pay myself about 7000-10000 per year or so, pay self employment taxes out of there and then contribute the remainder to a retirement account.

Establish your criteria, such as location, spending limit, kind of home, amenities, and possible rental revenue, in order to choose the ideal property.

That is certainly ideal for 4+ people in a house.

As others said 15-25K is ideal.

I see a lot of advice on financing and renting out homes, but ideally don't want to go that route if at all possible.