I'm not familiar witht hat bug and don't remember seeing it. However I have only played the original non-Skial version of the map.
Attached is the Stripper config, and here is a list of fixes and improvements.
Added an observer cam which follows the bulldozer.
Show the map's built-in round timer on the HUD.
Reset round timer to 35s when the bulldozer is defeated.
Ensured red win on round time end when the bulldozer is defeated.
Disable the round timer when an ending is chosen.
Added logic to make the driver of the bulldozer use insults belonging to their class.
Remove unneeded Announcer and Scout insult voice line ambient_generics, saving edicts.
Players who fall into the mortar pit are killed one minute into the round to prevent stalling.
The mortar pit damage is increased to kill self-healers.
Players can no longer be pushed underground by the descending construction elevator.
Players can no longer avoid ending teleportation by climbing the car park barrier.
The swinging crates are no longer solid, so physics projectiles cannot throw them off course.
Hitting the end button after the blue player has disconnected will no longer cause the server to crash.
Note that I had to add a .txt extension to the file to upload it.