Its become a hip-urban nook with 3 very popular breweries, restaurants, cafe's and a bike shop within 1-2 blocks, 1/2 mile easy access to I25 (interstate) and right on the main tourist route.  

If there isn’t any damage and you are able to immediately list it, I wouldn’t keep the security.  

Moisture is not good but if there’s no damage/corrosion of the live equipment then it’s not necessary yet and your better off dealing with the source of the moisture.

@Bruce Woodruff tactful ways in doing so to avoid him damaging the place further?

Potentially a mix of the data scraping taking into account blocked days on the calendar as true occupancy, and factoring fees as part of the ADR (average daily rate) I would say they have shown a material miss when it comes to data for properties that I had managed in the past.

Bad faith in uncovered damages?

The current owner started adding an additional unit to the property on the lower level by blocking off a wall and adding a shower however it remains unfished as it stands today.

Damage can be an issue.

Chicago is literally comprised of micro neighborhoods & communities, and the decision to invest in any given area must be determined on a house by house, block by block, basis.

Dishwashers can be high maintenance and provide another risk of leaks and additional damage.