I'm sure they have a policy on short term rentals.If you mean "legally" based on the terms of your loan (i.e. one for a primary residence), I would imagine that would be fine as long as you are living there.

I imagine there are property managers that specialize in section 8 housing. 

I would imagine the commission on land is lower, and might even be paid by the seller, but check the auctioneer's website or call them to be sure.You mentioned marketable timber on the property-how large is this tract?

Was pouring over underwriting last night to see how finance and investment people view these deals.  

I've been pouring through the Chicago Building Code and have found conflicting things in it, so your input is really appreciated.

It doesn't require a huge stretch of imagination to see the temptation.

You are looking for one deal out of 1,000s if the numbers look good with no money down imagine what the investor with 5, 10, 15, 20% down are thinking.Focus on getting 3.5-5% down live in one and rent the other units. 

@Tyson Dierschke, it sounds like you are a little scattered and want to do everything you can imagine.

As you can imagine, there are a number of ways to get leads. 

I'd imagine you have to break this down into smaller chunks other wise almost no one will be able to approach this.