The math says to perform $500 sewer clearing each year instead of $5000 excavation, but the $5k bought peace of mind.

Immediately, I performed a Roth conversion.

We've gotten that advice from an old timer in the trades, but Chicago is notoriously know for lagging with issuing permits and performing inspections.  

My wife and I have a few homes near campus we use as student rentals and they certainly perform well.

If the assets makes financial sense to keep otherwise, hiring a PM solves your problem and allows you to keep a performing asset.

Owners mistakenly ASSUME all PMCs offer the exact SAME SERVICES and PERFORM those services EXACTLY THE SAME WAY, so price is the only differentiator – so, they often select the first PMC they call or that calls them back!

Is there a move here, could you try to buy the non performing note?

I can count on one hand the number of times I've seen subcontractors on those job sites performing work.

The Cape also in my opinion is oversaturated with STR's so it's challenging to find a base number of how your property will perform. 

What is the experience of the group at performing this sort of development?