Likely, you would wait at least several years until that property had more value before you would exercise your option and the family continues to enjoy their dry home.

If shingles are broken or missing, leaking, rotting, etc, that's a defect.

After each flooding that has already occurred, if things haven't been dried out and addressed appropriately, there may be mold in the walls already.

I see tons of houses in Milwaukee that are left to rot in the inner city by out of state landlords who probably thought it was a good idea to buy a $25,000 house that rents for $800 and just hire a property manager to deal with everything.

As we are not seating on an un-limited cash pile, a few winning TS bids would dry up our fund. 

At our dry 8500 feet, how likely is it that there is mold?

Good multi-family properties in safe parts of Chicago are drying up quickly so I'm looking for every and any avenue to finds leads.

I would also get a good dry wood and subterranean termites inspection done as soon as possible.

I'm back on dry land next week.  

Dry runs happen, if they want to sell but want to sell at market price, I'd be forming a relationship with a realtor to pass them off too.