My leases clearly state that the "Tenant shall maintain all appliances, equipment, furniture, furnishings and other personal property included under this Lease". 

And if you include the suburbs the Milwaukee metro area has about 1.6 million people.

Open escrow with homeowner, end-buyer, and self; self transfers contract to purchase to end-buyer in Title/Escrow, and provides T/E with end-buyer's contract with self: agreement to purchase, and fee instructions for self ($10k + difference if any) to be paid out of closing escrow5.

You are better off waiting until this renter is out, cleaning the place up, and then showing it vacant.Your lease should include something about the tenant maintaining the property, you should inspect every 3-6 months, and you should have consequences for tenants that fail to comply. 

It's crucial to note that this does not mean the buyer assumes the loan; the original loan terms and obligations remain with the seller, which includes the debt remaining in their name.The bank's involvement is minimal in the sense that the loan is not officially transferred.

I’m a broker/owner that’s deals exclusively with investors in South Bend.

Would be ideal to try and qualify for §121 exclusion - which allows you to exclude up to $250k of gain for selling your principal residence ($500k for MFJ).

Does a full rehab include foundation?

Nice bit of self promotion!

If so, I would consider going forward with your plan but self-managing the condo for now for the sake of cash flow.