Josue Rivera Definitely check out what zoning restrictions if any apply.

Two types of upfront costs:- Before Closing:  Only thing that should be charged here is an appraisal, and most of the time this gets paid directly to the appraisal company, not the lender. 

Don't assume what a bank will do, go ask a few directly.

What advice would apply to the AirB&B portion of this scenario or where would y'all point me for further reading, advice?

Hi Flavius,Direct your realtor to ask for the seller to supply the permit.

I have no idea if such a law exists in Illinois and whether it applies to a 7 unit.The fact that you didn't deliver the $5,000 to him suggests that --- even if you had an oral contract --- it's too late to enforce it.

If you'll be here during that time and only be renting it in the super hot summer, you might have more trouble getting it rented.Hopefully that gets you pointed in the right direction.

@Joe E.My specialty is self directed retirement accounts, not financing.

And then start applying and taking action.Best of luck!

I wanted to update you both as to what direction we ended up going in.