The bank mentioned they can't finance investment across the border. 

Otherwise you're real estate gambling not investing.

I have been here since 1975 also with 29 years USPS..I tell out of area investors to stick to outer 322 zips that border 320 zips by 1 or 2.

Also, appreciation is somewhat of a gamble.

I grew up in rochester hills which borders pontiac.

Also, have you looked into surrounding markets on the border of Dane County?  

Like in gambling, the house always wins over time.

I'm an east-sider who invests in real estate near the MN/WI border. 

I posit that many of the things that investors do border on the unethical in at least a few peoples eyes (talking a seller into taking the smallest sliver of equity in exchange for their property so I can maximize my own gains sounds pretty unethical to me) and that the only person doing something actually illegal in this case might be the lender if they knew the intention of the buyer.

Appreciation is a gamble whereas cash flow helps with later financing (improving your income numbers) and is more of a guarantee even if there's really no such thing.