I would suggest that you interview several Realtors and ask them the following questions, to ascertain if they are truly Investor Friendly, or if they are throwing you a sales pitch.1.

@Lisa Hill,  I suggest you plug "Note Flipping" and/or "Jerry Norton" into the search window (upper right ) and there are several threads which address this question.

I would suggest the podcast webinars and the education tab at the top, its truly so much info its almost over whelming. but if you have any questions about anything investing please just ask people here are more then willing to help you out.AJ

Any suggestions on agencies that are willing to insure during the rehab process?

Plan would be to complete the simple renovations, find a quality tenant, then refinance to pay off the HELOC.

I suggest networking here on BP in some of the local forums.

Reality is they'll probably never sell this property as-is for 20k, but due to my involvement I know all the details to justify that cost.I'm looking for suggestions on if this deal could even happen, would anyone fund something like this in Illinois?

I suggest open communications with the sellers and tenants NOW and come to some sort of agreement.

Any suggestions on local groups?

@Leland Smith It is nice to talk about comps but I strongly suggest you begin by looking at YouTube videos on the Uniform Mortgage Data Program.