Resort workers show a routing problem headline, and because of that sometimes don't fix any broken objects.
After some research I found out this is because the workers what to stomp some roaches. But those roaches are in not reachable places, for instance under the ground (really under the layer of sand) or on top of a staircase.
Mods: No, mods where later installed to check what caused the problem.
Resort: The cheapest "abandoned" resort
Resort level: 4
Custom content (store): Yes but never near the misplaced roaches
Custom content (non store): No
I fixed it by removing the roaches using "testingcheatsenabled" when found