So that's what I plan to do: I'm going to buy in my own name and use a DBA.However, I also want to start building corporate credit now; which requires an LLC.

I don't have the cash required, so I'd have to finance.

Are the LLC's multi-member LLC's - If they are, they would be required to filed a separate partnership tax return.Your profile mentions that you are a real estate agent, you may want to see if you are eligible to claim real estate professional status.

The process must also be continually improved as new technologies come online, laws change, bottlenecks are identified, etc.

SBA , Smaller Banks it would have be Commercial Loan sure they require something down will be required unless you have some relationships already 

Anyone have any experience with Section 8 and their requirements for Condos?

Arkansas will be a lower ROI, but needs housing so that market would require more houses to make any gains.

But with zero enforcement since they don't issue or require STR permits.  

It would require tweaking but I suspect you could get close on a lot of it.......just something I have been thinking about for a while and a guy like you could probably create something pretty cool!!   

Start by educating yourself online or through courses on the house flipping process, renovation costs, and market analysis specific to Chicago.