The homes are in beautiful settled neighborhoods with best schools.  

That just isn't going to happen.If a tenant willfully wants to leave and wants to settle the obligation for the remaining term of the primary lease for a discounted amount then generally a landlord has prepared by an attorney an agreement to vacate,lease termination, and a settlement agreement.No legal advice given.

I'd settle for ruling my local area haha or at least owning a island.

If you strictly want to settle on SFR, looking out of state is a good option.

Don't settle for just the "dye test."

They might be looking at auction to settle the debt. 

As they settled in and started expanding their family quality issues arose as did the lack of space.

I think it would be easier when settling his estate so that is likely where he is coming from.

@Logan LarochelleIt is pretty standard to pay for such a matter out of pocket and then settle with your insurer - this is why you have an operational reserve in the bank.  

consider proximity to an airport wit reasonable fares,  Manty and Trivers (local speak) are a Hike to Milwaukee Airport, and Green Bay is quite expensive to fly out of. just a thought, Unless you fall into a great deal, a $50-70K 4plex is gona be pretty rough,  both in condition and location, get familiar with the areas, and if you do settle in Manty, Just remember its Cooler Near the Lake, not sunglasses and board shorts cooler, like 50 degrees in late June, and 20 miles west its 80 degrees. just considerations.