Did not include wife on the credit check ( although we know she works but is on maternity leave.) looks like a couple on a good 3 year trend in job progression but very rough past ( divorce, child support and some bad debt.) how much deeper do we dig ?

Any insurance agent can go in deeper with you.  

I believe I need to get a real estate seasoned attorney to delve into the specifics for Illinois.

As far as I know, it goes deeper than # of mortgages.

To ALL,Any suggestions on an what you may feel are excellent books or sites that really delve into creative financing?

That means don't pass on it yet, but you need to dig deeper before buying.What strategy?

It does not sound like you have such a Vendor, so you would be better off waiting for the auction - or for the property to fail at auction and be listed by the lender.If you are intent on trying your experiment, before wading deeper in the weeds , determine if the owner/borrower waived their right of redemption {if that is permitted in Ontario} or is past the redemption date?  

My partner and I want to dig in a little deeper, I.e.

I know it's a glaring hole in the calculations, but I am unsure how to calculate that into the initial review of a property's financials to determine if it's worth looking into deeper.

Anytime the guarantee is put front and center and is made to be the highlight of how a company sells property, you should definitely slow down and dig deeper.