I use a CPA, too, but I like to do my own bookkeeping throughout the year and send him a tax package quarterly to review.  

There is no "perfect" structure out there but I've tried a lot of different ones within QBO over the years and this is by far the best I've found.I use this structure for my own portfolio as well.Hope that helps!

Do you guys use hard money lender for a rehab or use your own cash?   

That means that bank has its own set or rules/guidlines and can offer exceptions and offer more programs. 

I get the desire to own outside of Chicago proper, but instead of going to another state altogether, why not invest in one of the burbs?

Owning real estate is not passive.

Maybe the section 8 person can help advise you, but I'm certain they will give a disclaimer with anything they say that you still need to consult your own lawyer or read the rules.

@Cody Baum - Can you become an investor focused agent and get practice in real estate without it being your own money? 

IF it was not on an auction site none of the information would be known unless you do your own research. they could say its a 3bed 2 bath home and you go buy and its burned down (seen that before). 100% is on the person bidding at auction.

I own a small multifamily commercial in Albuquerque and can confirm the diversity of the economic and cultural factors that you mentioned.