The Midnight Sapphire Hotel in Gray Zone Warfare isn't as relaxing as its name suggests, so you'll have to pay close attention if you want to complete Celebrity Crash or Dirt Digger.
Celebrity Crash // Dirt Digger | Gray Zone Warfare GUIDE | Mission Tutorial
The two tasks are one of many instances in Gray Zone Warfare where you have to choose which merchant to help, which determines what rewards you receive. This time around, you have to choose whether Banshee or Handshake receives a crucial VHS tape.
The VHS you need to complete Celebrity Crash or Dirt Digger can be found on the east side of the Midnight Sapphire Hotel area, in the Whitewater Villas section, at the map coordinates (174, 165).
The most direct route to this area is from the Hotel 1 Landing Zone, which is just a short walk northeast of where you can find the tape. However, if you haven't explored this LZ yet, you may want to venture further afield to a more distant LZ, which can also prove to be more dangerous with the added enemy NPCs.