Though first step, get the place.Family and friends still think we're crazy, but more frequently ask questions and for "our thoughts". 

They're out there, but picking up properties with enough equity that making it interesting to investors and borrowers are willing to walk away from is a rare thing indeed.To answer your question though, there are opportunities to pick up properties subject to existing financing by just paying the reinstatement fee (which are usually $thousands).  

If it doesn't affect my bottom line or vision for the overall project I will frequently defer to them and say things like "you are the expert - how would you handle this?"

Unfortunately, this is a frequent occurrence.

I am interested in wholesale deal, subject to, and lease purchase deal. 

I am currently in the process of educating myself on real estate investment through subject to and lease options; once I feel confident enough with knowledge I will reach out to you

You should definitely check out Brandon's book on the subject: http://get.biggerpockets.com/nomoneydown/

I am not aware of any laws in the Chicago/Cook cnty/IL area, but if you do it, perhaps do it on a point based system like an tenant applicant acceptance...so if you get sued you can prove it was objective and not subjective based on protected class status.

Individuals who change jobs frequently, but who are nevertheless able to earn consistent and predictable income, are also considered to have a reliable flow of income for qualifying purposes.   

I put my money where my mouth is too as all property I own are below market.It's a subjective balancing act though.